


Fates Collide

by existential1rony



Category: Chicago PD (TV)
Genre: Best Friends, F/M, Fate & Destiny, Light Angst, Past Relationship(s), Slow Burn
Language: English
Status: Completed
Published: 2020-03-17
Updated: 2020-06-21
Packaged: 2021-02-28 18:26:53
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 28,446
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23181700
Author URL: https://archiveofourown.org/users/existential1rony/pseuds/existential1rony
Summary: Sometimes your paths keep crossing with the people you're destined to end up. Jay and Hailey would be great partners in any life, there's no doubt about that, but what if there was something underlying to it before they became them? Sometimes the timing of things doesn't always work out, but what if colliding fates could help them align despite years that have past?
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 10
Kudos: 117





	1. Chapter 1

Detective Jay Halstead had been put through the ringer the past two years. First his ex-girlfriend and partner, Erin, left to join the FBI in New York without so much as a goodbye. Then one of his stray bullets ended up killing a little girl. Soon after that his PTSD nightmares returned and he started silently spiraling, which lead to him sleeping with the sister of a criminal veteran he was trying to stop; and then she turned out to be a drug-dealer (and a suspect in a murder of an undercover DEA agent) herself. Luckily, somehow Voight made Jay's involvement with her all go away; Jay didn't ask how and Voight didn't tell, but his boss did demand Jay go to therapy. He was hesitant at first, but he did it so Voight didn't kick him out of Intelligence, only completing the mandatory sessions though. Things slowed down a little after that until Al, his coworker and everyone's secret mentor got thrown in jail and killed there. Maybe Jay could have handled that had his father not been killed in an arson fire a mere few weeks after Al. Jay lost it then and got himself shot and almost killed trying to catch the guy who planned the fire. That was Voight and the rest of the unit's last straw, Jay was to see a therapist at least once a week now to try to get his recklessness under control. This time he actually agreed because he realized that ever since Erin left and his friend, Mouse went back to war, he really didn't have anyone to confide in anymore. Antonio was having his own clandestine issues it seemed, and his brother, Will, was also dealing with his own drama. Not that Jay confided in any of the above all that much anyway, but now it really felt as if he had no one. So therapy it was.

Fast forward almost a year and things for him had normalized a bit. He couldn't say the same for the rest of his unit, however. Antonio had vanished to check himself into rehab for an opioid addiction he developed from a busted shoulder. Adam had been thrown in jail on misconduct and obstruction, due to him and Voight trying to protect Antonio after he accidentally killed the man who kidnapped his daughter. And Brian Kelton, the Superintendent and newly-elected mayor who had been after Voight and the whole unit was murdered. Voight had looked like the prime suspect, but luckily they discovered Kate Brennan, one of the commanders had done it. This would have been great considering this also helped free Adam, but Voight was going to let Brennan commit suicide to avoid jail and dishonorableness, and Jay just couldn't stand by and let that happen. With Antonio gone now, someone had to keep some semblance of the moral code still going. Voight didn't like it, saw it as another way Jay was going off on his own again. But since he loved the detective so, he knew what had to be done.

Jay was nervous as he grabbed the handle of his boss's office. It had been a week since the whole Brennan ordeal went down and he knew Voight was still a little peeved at him. He took a deep breath and walked in anyway, now or never.

"Jay, sit down, this won't take too long, but I want you to grasp it." Voight said to him in his gruff voice.

"Everything okay, Sarge?"

"Everything's fine. I just wanted to make you aware of some of the changes coming to the unit."

"Okay."

"Well as you know with Antonio gone, we're a man down. Add into the fact that none of us were emotionally ready to replace Al, we're at least two short now. I'm bringing in a new officer who's been doing Undercover for Gangs. She comes highly recommended, but she's fresh, so I'll want you to show her the ropes."

"Of course Sarge!"

"With that said, you're now our most senior member and rank and I'd like at least one more on your experience level. Kevin, Kim, and Adam are all great, but they each only have a few years on the job. That's why I'm bringing in another Detective, and I'm actually making them you're new partner."

 _Here it is_ , Jay thinks to himself. "Why? So you can have someone keep an eye on me? I'll work fine with one of the other three; we've been together for years now. I've been doing the therapy, I should have earned your trust back by now."

"It's not that at all, Jay. I just think this unit will be stronger with two intelligent, experienced detectives leading the charge. And if she keeps you in line along the way, well, even better!" Voight gives him one of his rare smirks.

" _She?_ " Jay questions, not because he cares about the two new members being women, but because he's not sure how to feel about having another female partner.

"Yes, she. I've had my eye on her for a while, but I wanted it to be the right time. She has an exemplary reputation working undercover and for Robbery-Homicide. Actually, I've been told you two were in the same army battalion, so you should be used to working together."

Jay closes his eyes briefly as he realizes the _only_ person Voight can be talking about. He's about to respond when he notices his boss look up towards the door. The hair on the back of his neck stands up when he hears a voice he hasn't heard in nearly thirteen years.

"Halstead, it's been a long time!" she says with the same amount of sass he remembers.

The word slips out of his mouth before he can even turn to look up at her. " _Hailey…_ "

* * *

Detective Hailey Upton likes her life. She goes to work, she does her job, well, and she comes home. It's basic, it's simple, and it's all she needs. She'd been with Robbery-Homicide for a good amount of years now and as much as she sometimes yearned to continue advancing her career, she was content. It beat the hell out of going on year-long undercover assignments. And since she never quite got over her last one, she was hesitant to look for much else in fear that's what they'd want her for again. So when she got the call and offer from Sergeant Voight, she was intrigued to say the least. She knew her former best friend was on his unit. It's not like she stalked Jay, but Chicago wasn't _that_ big, especially the police force, to not know where he had ended up. Plus, the Intelligence Unit was the cream of the crop for their little city; she'd by lying if she said a small part of her wasn't proud of him when she heard he made it in with Voight's team, even if they hadn't seen each other in over a decade. Still, she wasn't sure if she wanted to resurrect that part of her past yet. She had done her best to bury it and leave it there. Regardless, there was a part of her that still felt drawn to him, and the way Voight explained the situation, she almost felt _obligated_ to be there for him. So with a heavy sigh, and a few huge glasses of wine, she called him back the next day and accepted the offer.

Now here she stands, staring at the back of Jay Halstead's short-cropped brown-haired head, the same exact cut as when they were younger. All of the memories want to rise at once, but she squelches them all down. Instead, she uses the tactic she's been so accustomed to since the army, firmness and sass.

"Halstead, it's been a long time!"

" _Hailey!_ "

She swears she _feels_ him say her name before she even hears it. Maybe this wasn't such a good idea after all. How is she supposed to look after him if she's not even sure she can trust herself around him?

"Actually, it's Detective Upton now." She responds a little too coolly, the smirk on her new boss's face along with the shock on Jay's makes her aware it held no hint of humor. So she decides to backtrack.

"I'm just kidding, Jay, how've you been?"

Not knowing what to do with her hands as she stands above him while he's still seated, she folds her arms. She gives him a small smile and tilts her head at him, hoping to reassure him of no bad blood, as she waits for his reply.

"I've been good. Wow, it has been a really long time. How have you been?"

Jay says as he finally stands up and leans in to give her a quick hug. It's awkward, no doubt, but probably just to the two of them. She's certain no one would notice, at least she's hoping not. If Voight does, he doesn't seem to acknowledge it.

"I've been good too. Excited for this new journey I guess. It certainly will be different from Robbery-Homicide."

"I'll let you two catch up. I got some paperwork to do. Jay, be sure to introduce her to everyone when they come in." Voight says to them.

"Sure, Sarge." Jay replies and nearly places his hand on her back, but hesitates, to lead her out of the office. She takes it that's their cue to scatter.

Jay closes Voight's office and it's now just the two of them in the empty bullpen. The silence envelops them both, neither sure which one of them should speak first. Finally it's Jay who bites the bullet.

"You want any coffee? I just made a fresh pot not too long ago." As Hailey raises her brow at him he continues on quickly, "…And before you say anything, I've upped my coffee making skills immensely since the barracks days."

"Oh, good, I was gonna say- Because your coffee tasted like crap, Jay! We swore you sometimes put actual mud instead of grinds in it. But I'd love some as comparison."

They smile at each other and head into the break room. He pours her a cup, grabbing the milk and adding just a small drop in just the way she likes it. They both try to ignore the muscle-memory of it all. Jay leans with his back against the sink and his arms folded as he waits for her to try. She takes a sip and he instantly gives her his _"well?"_ look.

She purses her lips. "Not bad! Definite improvement I must say."

"I'm glad to meet your approval after all these years…" he replies, drifting off.

"Yeah… it has been a lot of years…" she agrees. It gets silent again for a bit.

"Hailey—"

She instantly cuts him off. "Let's not, Jay, okay? Not now. I'm not here to rehash the past. Let's just think of this as a new beginning, the start of a great partnership."

He swallows and clicks his lips. "Alright, fair enough." He reaches out his hand to hers to shake. "To new beginnings…"

As she grabs his hand they both feel the pull and had never in their life been gladder than to hear joking and movement coming up the steps and into the bullpen. They instantly drop the other's hand.

"Guess the cavalry has arrived!" Jay whispers and signals with his head for her to follow him.

As they reenter the bullpen, Kim Burgess, Kevin Atwater, and Adam Ruzek are all draping their jackets over their chairs and getting settled in. Jay makes a dramatic _ahem_ to get their attention and all six pairs of eyes turn to look at the two of them.

"Guys, this is Detective Hailey Upton. She's going to be my new partner. Hailey, this is Kim, Kevin, and Adam."

Hailey goes to shake all of their hands and give a proper introduction. She can feel Jay's eyes on her as she gives them a quick background on herself and she tries to push down the butterflies she hasn't felt since what feels like another lifetime ago.

"So I met Jay in basic training, and we did our advanced together and even got in the same battalion until he became Mr. Army Ranger..."

They smile at each other when she briefly fills in the team how they originally knew each other. Their smiles are laced with sadness, but no one is none the wiser. She pretends not to hear Adam when he turns and whispers to Kevin while she and Jay talk to Kim.

"Damn, she's hot!"

"Mhmm, Jay's in trouble!" Kevin replies.

 _If they only knew the half of it_ Hailey thinks to herself...

* * *

_[A/N: While I was thinking of another one-shot to write before attempting two other extensive story ideas I had, this idea popped into my head, so I'm running with it. Obviously, it's slightly AU, but the core of their characters is staying. Also, in our world this takes place in Season 7's timeline, but it won't follow it extensively (if at all) Especially since we apparently won't be getting an appropriate ending to this season now. On that note, I hope you're all staying healthy and safe! The world is a crazy place right now, so I hope this and any remaining Upstead we get this season helps you through! Enjoy!]_


	2. Chapter 2

In Jay's senior year of high school, the world as he (and every other American) knew it, stopped. 2001 brought the worse terrorist attack ever on American soil. Thousands had died, including hundreds of first responders who tried to help. His parents were devastated as it affected them personally, losing one of their childhood friends who had worked in one of the Towers. His dad became even more unbearable to be around. It was a lot to deal with at seventeen years old. The shitty home life that Jay had already known only got worse. Jay couldn't just stand around, he felt he owed it to his country to help in any way he could. The urge in him to protect others only got stronger. So at nineteen years old he finally worked up enough courage to leave his poor mother and enlist. Thousands of others his age had done the exact same thing the past couple years. He intended to leave Chicago and never look back.

It had been a typical day in basic training, he was getting used to the strict regimen and vigorous workouts. But most importantly, he had started to form bonds with some guys that he just didn't have back at home. He connected more with the people who joined. He had just grabbed his lunch and was sitting in the Chow Hall with two of his new pals, Mouse and John, when he noticed a very pretty blonde sitting with a brunette. He'd been here a few months now, but had never noticed her before. They were probably a couple years younger than him, which seemed to be a pattern since he didn't join straight from school. He didn't know why, but he felt the need to go introduce himself to the blonde. He poked Mouse's side to get his attention.

"Hey man, I think I'm gonna go ask to sit with them." He nods his head in the girl's direction.

Mouse and John instantly laugh at him. "Yeah right! Talk about out of your league! Let me know how that works out for you." Mouse scoffs.

Jay's never backed down from a challenge. "I will."

He grabs his lunch tray and stands up, making his way over to their table. As he gets closer, he feels his nerves tick up a notch, but tries to ignore it. When he arrives, both girls look up at him curiously. He suddenly freezes and looks at _her_ specifically like a deer caught in headlights. She looks amused.

"Would you like to sit? Or are you gonna stand and eat your food hovering over us?" she asks.

Her words bring him back to reality and make him feel more at ease instantly.

"Yes, thanks." He says as he finally sits across from them. "Halstead, Jay." He reaches his hand out to shake as he introduces himself. She grabs hold and smirks.

"Upton, Hailey. Are you always this serious, Jay Halstead?"

_Is she teasing him?_ So much for him winning this challenge... He smiles back.

"Not always, no. Guess the army's making it more of a habit."

"Well Jay, this is my friend Olivia. What brings you over to our table?"

Olivia shakes his hand and they both give him full attention. He can sense Mouse and John's eyes staring at the back of his head.

"I haven't seen you around, so I thought I'd come introduce myself. My friends over there can get a bit repetitive day in and day out."

"So you came here because you were bored?" Hailey tilts her head and lifts her brow at him. She's definitely still teasing and Jay knows he's in trouble.

"No, no of course not. It's just, not every day we see girls as pretty as you in the barracks."

"Aww, look Olivia, a guy after our own heart!" both girls crack up and Jay blushes.

He can't believe he's going to have to return to Mouse 'striking out.' He's enjoying her sass, but he's not sure if he made the right move coming over.

"Look, I'm sorry if I bothered you guys, I'll go back to my friends now."

He's about to stand from the bench when Hailey grabs his wrist. "Jay, Jay, look, if you want to hang out with me, you're gonna have to keep up, alright?"

He's shocked at her words and even more so when she waves and signals for John and Mouse to come over. Jay nods an okay at her as both guys make their way over and introduce themselves. Jay slides down, making sure to make room for them, but still be able to sit directly across from Hailey. With the whole group around the ice is broken more and everyone starts to socialize. Jay is fascinated by Hailey; she's unlike any girl he's ever met. She's funny, but also looks like she won't put up with any shit. It's refreshing from all the stuck-up, self-absorbed girls he went to high school with. Not to mention, even with no makeup on Hailey could run rings around all the ones he knew that caked it on. He's glad for Mouse being a goof and amusing Olivia and John, and takes it as his opportunity to get to know her better since they don't have a lot of time.

"So Upton, where are you from?"

"Where do you think I'm from?"

"You really enjoying messing with me, don't you?" I grin at her.

"I do."

"Alright, I'll bite. You seem low-key enough that I doubt you're from one of the coasts. But you also seem worldly and a little more fast-paced, so I doubtful you're from a small town. Definitely a city. You don't have an accent, so you're not from the south. But you have a hint of a tan, so maybe somewhere like Arizona? How am I doing?"

She gives him a big smile and he feels like he won the lottery. "Not bad. You definitely hit on some key points. The tan is natural actually. I'm from Greektown in Chicago."

His eyes almost bug out of his head. "Shutup! I'm from Chicago too, Canaryville. Mouse is also from Illinois."

For the first time in their whole exchange, Hailey looks speechless, but she recovers quickly. "Now that you mention it, you do look like an Irish momma's boy."

They crack up. "So do you guys really say, 'Opa,' all the time and put Windex on everything?" He jokes back.

"No, but that is now my mom's favorite movie."

"And what's yours?"

She hesitates. "American Pie."

"Hailey, I think this is going to be the start of a beautiful friendship."

"Woah there, Halstead. Let's not get ahead of ourselves here… but I think you're right."

They start grinning at each other again when they hear the drill sergeant yell.

"TEN-HUT…"

They all stand at attention and get ready to leave. Hailey gives him one last smirk. For the second time in just a couple of years, Jay's life infinitely changed. And for once he couldn't be happier…

* * *

_[A/N: Thank you all so much for the kind response and words. It makes me happy that I can help with distractions in this time of need. Apologies for any army inaccuracies (now or in the future), it's not my forte. I must say, I'm shocked there aren't a lot more fics since this whole world mini-quarantine started. It's a depressing time, I get it, but you'd be surprised at how much writing/reading can help. It's a great outlet to focus on while your other faves are on hold. If you've never written before now- maybe give it a try? It can be therapeutic. I know I'm probably a nobody to you, but this fandom has connected us all, and with everything going on it's the perfect opportunity for the world to connect too. Focus on the positives as much as you can and take care of yourself and others!]  
_


	3. Chapter 3

It had been a few weeks now since Hailey had joined the team and been officially partnered with Jay. Everything had been going well thus far, the unit had been swamped with cases, so it was enough to keep their minds busy from their personal history. Still, as much as things had changed, so much felt the same. They were still keeping the other at arm's length and treading lightly, but their banter came back easily. Hailey fit in with the team well too, they all enjoyed the extra sass and couldn't argue that without Al and Antonio around anymore, a more-authoritative personality helped balance things once more. Also, it seemed like Jay was starting to seem happier again for the first time in years. And Hailey hadn't felt this type of camaraderie since she had left the army. While they weren't voicing it yet, Hailey and Jay were incredibly grateful to find their paths had crossed again.

Which leads into today, the unit had a lighter day than normal so they all agreed to meet up at a bar to wind down and get to know Hailey, and their newest recruit, Vanessa Rojas, better. Jay took it as his opportunity to finally get some alone time with Hailey outside of work and suggested they meet earlier for dinner to catch up. While she hesitated for a moment thinking it over, she ultimately agreed. So now they were sat at their high-top waiting for the waitress to take their food order and sipping on their drinks.

As Hailey puts her menu down Jay asks, "Let me guess, you want to split an order of wings, and then you're getting a chef's salad with extra ham and olives?"

They smirk at each other. "Am I that predictable?"

"No, I just know you, Hailey Upton."

"As much as you know I hate to say you're right, you're right… with the food. As for me though, it's been years Jay, maybe I have some surprises up my sleeve."

"I don't doubt it." He replies as they smile at each other and take another sip of their drinks.

They get quiet for a bit, but it doesn't last long as the waitress comes back asking what they want. They take it as their opportunity to regroup.

"So, what's it like living with Rojas?" Jay asks.

Voight had brought Vanessa on a week after Hailey had joined, recruiting her and Jay to take the younger officer under their wing and gage their opinion. She had a lot to learn, but was good police. Later that week Hailey had realized Vanessa had no place to officially live since her last undercover assignment had ended, and since she had a spare room she offered it up to her. After all, both were new to the team so they may as well try to fit in together. It would be good to have someone close outside of her extensive history with Jay.

"It's not bad. We're always so busy with work anyway, so it's not like we get in each other's hair at home too much. And she's definitely still living the younger, party life. Always going out to the bar and trying to get me to join. She actually reminds me a lot of us when we were much younger, idealistic but hard working."

"Yeah, she seems like a good egg. And it's nice to have some fresh blood again. The unit has been through a lot." Jay takes another sip of his drink and Hailey studies him.

"So I've heard… so how are you dealing with it all?"

Jay takes a minute to process the question and his answer. For anyone else, it would be an automatic, "fine" …but this wasn't anyone else, this was Hailey, and even though it had been years she still made him want to be honest.

"It's been a rough few years, well, you know, a rough decade is more like it… but I'm getting through it. Voight forced me into therapy last year, so that's helped a lot. Still, it's been hard not really having anyone I'm very close to anymore. I mean Will tries, but he's always so busy at the hospital and with his own life."

Hailey's eyes go wide then. "Wait, you and Will are close again?"

"Yeah, kind of. We broke the ice when he returned to Chicago for good. So we're infinitely better than we were."

"Oh, that's great. I'm happy for you. I know how angry you were that he refused to come back fulltime to help your mom while we were stationed. Speaking of, I'm so sorry about your dad… I found out a couple months after it happened and I just wasn't sure if I should reach out or not, but I should have, I just…"

Jay cuts her off and reaches out to grab her wrist. "Hailey, please, don't be! You didn't owe me anything, and you know my dad and I never really got along anyway. Which reminds me, thank you for the nice letter you sent after mom…" he can't bring himself to finish the sentence. "…I really appreciated it, and certainly wasn't expecting it after everything, but it meant a lot."

"Of course, Jay! I just wish I wasn't still stationed overseas at the time… I would like to think I would have been there if I could."

"I'm sure you would have, and you know, I wouldn't have deserved it."

"Jay…"

It's Hailey's turn to try to grab his wrist as he pulls back, but as if Father Time sensed the uncharted territory of the conversation, it's then the waitress walks over with their wings.

"Saved by the Bell!" Jay jokes, trying to lighten the mood and switch gears.

Hailey rolls her eyes. "You always did love Kelly Kapowski."

"C'mon. Tiffani Thiessen was a babe. And you're one to talk, Miss #1 Zack Morris fan."

"Hey, that was practically the only sitcom in color that played reruns over and over again while we were in Turkey." She pouts in defense.

"I enjoyed our marathons thoroughly, I'm just saying, pot – kettle." He replies.

"Alright, truce! We were clearly both dorks."

They grin as they bite into their wings, enjoying the lighthearted moment.

"Speaking of bubbly brunettes, how's Olivia? Are you guys still in touch? She went back to Cali right?"

Hailey smiles at the mention of her good friend she wished she could see more. "Yeah, she's doing great. She did go back home after we got discharged. She's married now, to Bobby no less, and they have two little kids."

"Get out! I thought those two would never get their act together."

"Yeah I guess they finally let go of their fears and realized how good they were for each other…"

She drifts off, it hitting both of them how close to home it sounds, as their eyes lock together. They feel the tension and try to push through it; Jay breaking the moment first.

"That's awesome. I'm happy for them! So what about you, any special someone in your life?"

She hesitates before answering. "You know how it goes, this life, especially so long undercover, doesn't leave much room for meeting guys."

"You're still incredibly aloof about your personal life." Jay's lips twitch up as he brings up the memory questioningly.

Hailey remembers him asking her this exact thing ions ago so she grins and replies in the exact same way, "I'm not aloof, I just don't have one…"

They both smile and bask in the recollection together as Hailey continues. "There was somebody a few years … but it didn't work out…" Hailey's eyes turn a darker blue and she quickly looks away focusing on the bar and avoiding his gaze; a hint that it's something she's not comfortable with so Jay decides not to pry anymore. After a beat she collects herself and normalizes again back to the Hailey who's so well at concealing her emotions. "What about you? Weren't you dating your partner at one point?"

Jay's brows shoot up in surprise. "Keeping tabs on me, Hailey?"

She gives him a small, sad smile. "Mouse and I got together before he went back in. I made him promise he wouldn't tell you that we hung out, you were already angry with him."

Jay laughs. "Yeah, that sounds about right. Of course he would tell you about Erin. I guess you can say things just didn't work out there either. I realize now we just weren't meant to be, we had the physical, but emotionally we were both so different, still it killed me then before I realized that. Her mom got into more drama and the FBI in NYC wanted to recruit her, so she killed two birds with one stone and left without much of a goodbye… poetic I guess, right?" he looks at her regretfully.

"Jay, it's water under—"

"Hailey, I—"

They both speak at the same time and Jay's about to let Hailey continue because he knows despite what she says, she's probably not over their past and he doesn't blame her. However before he can let her go on they hear yelling at the entrance and Adam's voice rings through most as the rest of their team walks over.

"Alright, Alright, Alright! Friday's are for drinks, let's get this party started!"

"Saved by the bell?" she whispers smiling.

Jay reciprocates it, internally upset his alone time with her is cut short as their table gets flooded by Adam, Kevin, Kim, and Vanessa. The two girls take the seats next to them as Adam heads to the bar and Kevin grabs two more stools to bring over.

"Alright Hailey, spill it. We want all the embarrassing stories about young Jay." Kim says.

"Oh, where to begin?" Hailey grins and rubs her hands together.

"Alright, let's not forget two can play this game." Jay warns.

"Bring it, Halstead!"

"Oh, this is gonna be good!" Kim replies excitedly.

"Hey Ruzek, get some shots!" Vanessa yells out to Adam.

"On it!" he screams back from the bar.

"Oh, I like you two girls already!" Kevin jokes.

They all crack up, knowing they're in for one fun night. The hours fly by as they all reminisce about the unit's past and Jay and Hailey's; and for the latter, it feels just like old times again. Hailey becoming gladder by the day she agreed to take the job and Jay forever grateful he's gained a second chance...

* * *

_[A/N: So we're chugging along, with this story and with life. How we feeling? Any theories? It's been a fun one to write so far. I hope all of you are staying well, staying sane, and keeping positive. Thank you so much for all of the kind words and reads. It always means a lot, but somehow in these trying times it means more. Until next chapter, take care!]_


	4. Chapter 4

Hailey had been in the army for nearly a year now, which meant she knew Jay almost as long. Having these routines and regimental lifestyle had been good for her. And of course, being away from home helped in and of itself. But by far the best thing out of all of it was the friendship she had developed with Jay, and Olivia. Hailey didn't have too many close girlfriends back at home, between growing up around two older brothers turning her into the tomboy that she was, and just not wanting to bring anyone around her dad; it didn't allow for many. And as for her male friends, once puberty hit and she clearly started growing more into her looks, they all just started treating her differently. Instead of wanting to play ball or any of their other physical activities, they wanted to do something else entirely physical with her. She did have a boyfriend senior year, but that had ended in epic fashion once he started to realize her army aspirations. So because of all of this she was incredibly thankful for meeting Olivia, Bobby, Mouse, John, and of course, Jay. They had definitely become her best friends, none more than Jay. The two of them found a way to make each other laugh despite the darkness that surrounded their youths, and somehow trusted the other enough to open up to them more than anyone else. In fact, one conversation in particular a few months ago really solidified their deep bond.

"So, you never did tell me why you wanted to join the army, outside of 9/11 of course. It's still not too common to see girls join, certainly for our positions." Jay asked her quietly outside their bunkers while they sat on some nearby brush.

"Well outside of wanting to help people and protect those I care about, it also just felt like the right move. My dad wanted me to go to U.C. to become a lawyer, but man, I don't know, it just didn't feel right to go off to college and party after all that happened to this country a few years ago. We should be better than our pasts."

Jay smiles softly at her. "Yeah, I get that."

"It was more than that though…" Hailey looks down at the ground and whispers it so quietly that Jay almost didn't hear her.

She takes a long pause, appreciative that he's being patient for her to continue. "My family life was never all that great. And I knew once I became old enough I just had to get the hell out of there. Don't get me wrong, I adore my brothers. They'll always be my best friends. But they're a bit older and had already escaped and started on their new lives. It wasn't easy living with my dad… he, he used to drink a lot, which made him angry a lot, and he would take it out on my mom… physically. And sometimes, on us, especially when we tried to defend her, for defending us. And yet, no matter what he did, she still stuck by him, would never leave. They say God only helps those who help themselves, I guess. And I love my mother, I do, and my dad, I mean, they're my parents. But I just couldn't hang around to watch it anymore, even if he's tried to get better over the years."

There's a long silence when she finishes and she can see Jay studying her out of the corner of her eye. His expression shows surprise, but also overwhelming empathy, and surprisingly no trace of pity- which she loathes. She appreciates it, but she takes his silence as awkwardness, which she didn't mean to cause.

"I'm sorry, that was a lot to lie on. I'm actually not sure why I even told you, I never tell anyone. So let's just pretend I joined the army for only the first portion of my answer." She says while averting her gaze from him again.

Jay snaps out of his trance, so in awe of this strong, beautiful, funny girl who takes care of everyone around her and now who apparently has held so much in. He's never felt more connected to her. He quickly reaches out to grab her hand, wanting to reassure her that she can always open up to him.

"Hailey, no, I'm sorry. I'm so appreciative you shared all of that with me. Your childhood sounds like it was rough and yet it amazes me how awesome of a person you've become despite all of it. And in a way, I can understand…"

It's his turn to pause and her eyes go a little wide while waiting for him to continue.

"My dad is a prick too. Not like yours in terms of physical abuse, but he drinks a lot also and the verbal and emotional abuse to my mom is appalling. In a way I've now accepted the fact that I'll never be good enough for him, but my mother is a saint, and the fact that she has to put up with him angers me so. She's actually why I didn't join straight after graduating. I couldn't bear to leave her alone with _him_ , especially while my brother was already off at college. But eventually, like you said, there comes a point where you just can't stay in that house anymore…" his voice drops as he says the last part and his eyes look down to their joined hands.

They stay quiet for a while, allowing their revelations to settle in the other's mind. Their thumbs stroke over the top of each's hand allowing the brief moment of comfort they've never had from anyone else. Finally Hailey breaks the silence.

"I guess we're both pretty damaged, huh?" she turns to look at him again and their eyes bore into each other.

"Maybe." Jay smiles sadly. "But they do say damaged people make for the best stories." He bumps her shoulder with his.

Hailey chuckles. "Well, there's a positive spin I never thought of before."

"I aim to please."

"I think this was enough gloomy talk for one night, don't you? Can we just go back to you making fart jokes again?" Hailey teases.

"You know I'm down. In fact, I just ripped a juicy one, you'll probably want to cover your noise soon."

Hailey drops his hand and shoves his shoulder as they both crack up. Forever grateful they've found someone else to dig deeper under the surface with, but also goof off like they finally don't have a care in the world.

* * *

Hailey and Olivia are sitting on Olivia's bottom bunk browsing through a magazine and enjoying their brief break. They had all just finished their Advanced Individual Training and would find out on Monday where they'd get stationed and if they'd be together.

"I can't believe it's almost been a year." Olivia explains.

"I know, it's pretty crazy." Hailey replies, flipping the page over.

"What's even crazier is that it has been almost a year and you haven't slept with Jay yet!"

Hailey rolls her eyes. Olivia has been incessant with teasing her friendship with Jay since it started. She usually tries her best to ignore it and doesn't understand why she singles Jay out of the guys. Of course she's the closest to him, but a guy and a girl can be just friends.

"Would you stop that already? He's like my brother!" she tries to explain.

Olivia drops her magazine and gives her a sardonic look. "I didn't know you were in the Royal Family… do you want to sleep with all of your brothers?" she jokes.

"Shutup!" Hailey laughs. "You're one to talk, you're always hanging around Bobby. Your voice may as well purr when he's around."

"You see Hails, there's the difference between you and I. I have no problem admitting that one drunken night I'll be ripping all of Bobby's clothes off. You, on the other hand, act like you're not even attracted to Jay."

"Because I'm not!" Hailey tries to sound adamant, but even she knows it came off a little weak, causing Olivia to shoot her another look. "Olivia, please! What Jay and I have is good. We understand each other. He's one of my best friends, something I don't take lightly as you know. There's no need to complicate things."

"Whatever you say. I'm just saying, sometimes an itch becomes too hard to scratch. And sometimes, only one person has the right nails for it…"

Olivia simply states and turns back to her magazine, leaving Hailey's mouth slightly open in shock. She loves her friend to death, but her and Jay in _that way_ is just something she tries not to think about. What they have is too good to mess up. She repeats it like a mantra in her head, hoping to convince herself of it.

It's easier said than done when the group of them is hanging out at a restaurant bar hours later. Mouse and John went up to the bar to try to hit on some girls, while Bobby took Olivia over to the dart board, leaving Hailey and Jay alone at their table for a bit. She watches him take another sip of his Budweiser and can't help herself from wrinkling her noise at it, an expression that of course he catches.

"What's with the stink face?" he asks smirking.

She grins back. "I'm sorry, I just can't believe you're drinking Budweiser. Gross!"

"And what would you recommend, Upton?"

"Me personally, I'd probably go more with a Stella Artois." She says with a tinge of a fancy Dutch accent.

"Wow, you're really uh, oh, what's the word, De Snob!" he jokes.

"The Lake Forest in me is escaping …"

"What? I thought you were from Greektown?"

"Just a story I tell in bars…"

They grin at each other and Jay teases back. "Oh, all the bars that Miss 19-year old Hailey Upton has been in?"

"Hey! By next week, it'll be legal age-wise for me to drink in a bar in whatever country they send me to."

"Fair enough… so, Lake Forest huh? That explains a lot."

She rolls her eyes. "We left there when I was eleven. That's when my parents opened the diner. They thought it would calm things, not having my dad all buttoned-up executive-stressed anymore…"

Hailey feels herself about to be immersed in horrible memories, but thankfully Jay recognizes her trigger and hits her knee with his.

"So, first official legal drink, tell me what you're getting? I turned 21 right before coming here, so Will came back for a quick goodbye to take me out and be a, and I quote: 'proper older brother'" he uses his fingers for quotes to add effect. "Son of a bitch got me loaded on 'Four Horsemen,' swore it's what everyone drank for their 21st. Picture this, eight double-shots of Jim Bean, Jack Daniels, Jose Cuervo, and Johnny Walker all mixed together. I spent half the night over the toilet in a doorless stall in a dive bar in Canaryville while these old, Irish drunks pissed by my head and Will hit on some girl twice his age. Good times! So I hope your first time is better than that." Jay beams at her.

Hailey laughs, knowing full-well he told the story to keep her in the present and out of her own head and incredibly grateful for the amusement. She felt the familiar butterflies in her stomach that were starting to come anytime he made her laugh or got protective of her and she tried like hell to push them away. _What we have is too good to mess up_.

Needing to get out of her thoughts again, she finally responds. "I don't know. I haven't thought about it too much. Maybe an Old Fashioned? Our bartender, Nikki, at the diner used to make them a lot and the way he did it always looked so cool and sophisticated."

"Bourbon, Hailey? I knew you were a girl after my own heart!" he playfully cheered her soda with his Budweiser.

"Speaking of girls… Why aren't you over there with Mouse and John trying to get some?"

"Because I'd much rather get put in my place by you. Besides, this may be our last night together for a while depending on where we get stationed and I don't want to waste it on girls that don't matter."

He looks at her honestly and she has to glance down at the table to avoid his piercing gaze. _What we have is too good to mess up. What we have is too good to mess up. What we have is too good to mess up._ She keeps repeating the mantra over, hoping it sticks, and knowing if she says it enough she'll almost believe it. As if sensing her thoughts and the tension he caused, Jay continues on.

"Besides, we now have to make a list of beers besides Stellaaa Artoisssss that I can order if I don't have you with me. You can help me impress the ladies for next time. Although, I'm really hoping we get stationed together. You smell infinitely better than Mouse!"

"Me too, Jay, me too."

They smile at each other, both trying to slow down the beating of their hearts. Neither realizing they'd be okay with something more, but both too scared to admit it… even to themselves…

* * *

_[A/N: Just a little more background to their past. Figured I'd delve more into this story instead of my episode-based one while I try to wrap my head around the fact that we've seen the last of Hailey for this season. We had such high Upstead promise for Season 7, but I guess on to the next with more hopes due to these unforeseen circumstances! In the mean time, I'll do my best to continue writing to fill my Upstead void, and hopefully yours too. Much thanks and stay well!]_


	5. Chapter 5

It's been almost six months now since Hailey agreed to take the job from Voight. Since then her and Jay fell right back into their old friendship, as if years and distance had never parted them. There had been no one happier than Voight himself. For the first time in seven years he felt like Jay Halstead's head was fully on straight. Sure, Jay was still wired through his heart when it came to certain cases, but gone were the days of making foolish moves guided by anxieties and past traumas. He had figured Upton would be good for him and keep him in line more than Mouse or even Erin ever did, and he was right. The two were like a well-oiled machine. Their partnership was guided by mutual respect, trust, loyalty, and an incredibly deep bond that everyone could tell meant more than Jay or Hailey would ever discuss. So when it came to a case of multiple bomb threats and their primary suspect was a Muslim affiliated with a local mosque, Voight didn't hesitate to send his two best detectives to pick him up and scrub down his house. There were no thoughts in his mind at all about PTSD rising up again. He'd never seen Jay more at ease than he has these past six months.

After the bomb squad cleared the suspect's door, Jay and Hailey breached the house and tactically started looking around. They cleared the first floor when they heard movement in the basement. Jay signaled to Hailey to stay quiet as they slowly made their way down the steps. When they got down there was a woman in a burqa who hollered out in fear and coward in a corner.

"Chicago PD, let me see your hands." Jay called out to her while pointing his gun.

The woman just yelped in fear even more.

"Show us your hands now!" Hailey yelled out.

"Everybody clear the area, possible offender with a bomb." Jay said into his radio before he starts yelling at the woman in Pashto.

She responds back and Jay commands her again in warning before Hailey raises her hand to Jay to try to calm him.

"No, no, hold on, hold on, Jay, hold on. Wait wait wait." She says as she slowly starts approaching and leaning down to the woman, also putting her gun to the side.

"Hailey, stop!" Hailey, what are you doing?" Jay pleads as he sees her getting closer to the scared woman.

Hailey just holds her hand up to Jay and continues to speak to the woman. "We're not gonna hurt you. We're not gonna hurt you, okay?"

"Hailey. Hailey! What are you doing? She might have a bomb, what are you doing?" The desperation in Jay's voice becoming even more apparent the closer Hailey gets to her.

"We just want to see your hands. Can you put your hands up?" Hailey says as Jay yells in Pashto again.

When the woman still doesn't comply, Jay screams, "Hailey! Get out of the way!"

"Just wait, hold on!" she yells back to him and signals. "We're not gonna hurt you, okay? Let me just see. Let me see." She whispers as she gets right up to the woman.

"Hailey…" Jay warns again.

Hailey reaches her hand to the woman's burqa and pushes it aside, uncovering an infant the woman was trying to protect.

"It's a baby. It's a baby, okay? She's just scared…" she softly tries to calm Jay.

Even though he's easing up some, he's still not fully sure. "Show us what's underneath!" he tells the woman again.

"Hold on. She's scared, Jay. Hold on! Okay, It's okay." Hailey whispers as she pulls the cloth back all the way and the baby starts crying. She turns to look up at Jay as they share a look. "She's unarmed." She says as he finally lowers his gun. She continues to try to calm the woman softly while staring at him and hoping to ease his nerves as well.

A couple minutes later the rest of the team arrives and Hailey yells out that they're all okay. Jay runs his hands through his hair and breathes in deeply as he makes his way back up the stairs, Hailey following behind, gently guiding the woman with her. The team gets her situated on the couch with her baby as they start going through her husband's belongings in the living room. Jay was hanging back in the kitchen trying to calm the risen anxiety when Hailey made her way back over to him.

"You okay?"

"Yeah, I… yeah. You?" he smiles kindly at her.

"Yeah."

"We're not mind readers, Hailey. We didn't know what was underneath that burqa."

"I know. Until we did. Until we saw it was a baby." She replies gently.

"Well, not necessarily…"

"She's not gonna hurt her own child."

Jay shakes his head slightly. "I have seen it happen…" his eyes plead with hers.

"I know… but you're not in Afghanistan anymore…" she whispers calmly, reaching to put her hand on his arm when Kim walks over to them interrupting the moment.

Kim tells them the woman is actually their suspect's sister and everything points to her being clean and not affiliated with anything connected to the case. She was just trying to protect her child when she heard the door getting burst into. Hailey nods at Jay and he just nods back, signaling they'll continue their conversation later. They all wrap up in the house back to square one and head to the district to brainstorm some more.

* * *

The case finally ends a couple days later when they found out the person behind all the threats was actually a U.S. veteran himself suffering PTSD. In a standoff with the unit, he ended up killing himself, which devastated Jay because he thought he could get through to him. Hailey had recognized how much this case affected Jay and offered him to come over for drinks. The two had been good about normally unwinding at a bar, but since Vanessa was going to be out for a while and this was such a serious topic for them, Hailey thought _what the hell_.

After a beer down and a while of comfortable silence just staring at whatever game was playing on the TV, they started to delve in on the case. Hailey knew she had to get Jay to open up so this didn't eat him alive.

"You know this isn't on you, Jay. He was too far gone, nothing you said could have brought him back." She breaks the ice and looks at him sympathetically.

"I get it. I just wish I could have seen it sooner…"

"If it's on you, then it's on me too."

"No, you had the open-mind, even the other day with that woman and her baby. A lot of horrible things happened after… after I joined the Rangers. And I know I can't just like flip a switch and turn that off. But I do the work. I've learned to deal with the triggers, the stress… the war was apart of my life, it's not who I am, not anymore. I just had no idea I had any anger, or bias… We signed up to serve to help people, all people in need. I thought I could separate the things I saw and did over there, not carry back any preconceived notions…"

Hailey puts her beer on the coffee table and touches his arm reassuringly. "Hey, you just saved 30 lives. 30 Muslim lives. You put your life on the line for strangers from all over every day. You're a good person, Jay. Don't let memories of Afghanistan take that away from you."

"Thanks Hailey. You've no idea how much I've missed this… us…"

They share a knowing look and smile before Hailey silently swallows her emotions and changes the subject slightly.

"I can't imagine how rough it must have been over there. When I was in Kuwait there were some pretty gruesome things, but nothing like you must have gone through." Hailey says solemnly.

"Yeah, it certainly was no picnic. But fortunately having Mouse there too helped a lot. It was good that we had our history to get through it together."

"I'm still shocked he wanted to go back, but also not, you know? He told me you fought him on the decision. He said despite all the horrible stories you both had, he just couldn't sit around doing nothing. There was a part of him that will always belong to that life. They need his technical skills, you can't find many like Mouse with that devotion."

"No, you're right. I didn't understand it then, but I'm happy for him now. Becoming a cop just would have never satisfied him like it did for us. I just hope his current tours are less painful…"

Hailey tilts her head and angles it on the back of the couch cushion to study Jay while he looks down and fiddles with the paper on his beer bottle. "Do you want to talk about it?" she finally asks after a long silence.

"Nah, not tonight. I'd rather just enjoy my time alone with my partner." He forces a little smile and she nods.

"Okay. But Jay, know that any time you need to, I'm here."

"I know!" he hits into her shoulder with his as she raises the sound on the game again.

They've made it through most of it with a couple more beers finished and the sandwiches and snacks they had ordered completely diminished. Jay quietly ponders to himself, truly so happy to have Hailey back in his life, but still not certain he deserves it. He knows she means everything she says and it weighs on him whether he should open up like she asked. He owes her that at least, and it's one of the many things that made their friendship so perfect the first time around. After much internal debate, he speaks out again out of nowhere.

"It was the kids that were the worst…"

He says it so excruciatingly low that it's almost not audible. But she must have heard because she's quickly lowering the TV and giving him her full attention again.

"When I said the other day that I've seen mothers use their own children… I meant it. And not just that, sometimes it was us, a kid accidentally getting in the way, being in the wrong place at the wrong time, our screams of warning falling on deaf ears since they couldn't hear over the rapid gunfire anyway... It doesn't haunt me like it used to, but that's what I relive when it does…"

He sees the tears of sympathy well up in her eyes for him before she responds. Normally he would despise pity, but not with Hailey, with Hailey it was always just pure empathy.

"I'm so sorry, Jay. I can't even imagine. My experiences don't even come close to that. I don't know how you went through so much, especially during that time with your mom and all."

"It was probably worse coming home; the numbness of it all being over. But the therapy helped a lot. I got through it then because I told myself it was all for the greater good. Silver linings and all. Also, I let my memories of you carry me through any of the really dark nights…"

He turns to look at her again and finds her staring back curiously, nervously. He has no right to, but he says it anyway.

"Especially our last few days in Germany together…"

He watches her close her eyes and push her lips tightly together as she takes a deep breath, as if trying to control all of the emotional memories his words bring.

"Jay…" she timidly says, whether in warning or wanting to tread lightly with this conversation, he wasn't sure.

He opens his mouth, waits a beat in thought, unsure how to continue, but wanting it to be right. "Hailey, I…"

It's then they hear the front door slam and Vanessa yell, "Whew, thank God for Ubers!"

Jay and Hailey jump back from their semi-hypnotic state and move slightly away from the other as Vanessa makes her way into the room.

"Hey guys, how's your night? All you've been drinking is beer, seriously?"

Hailey looks up at her roommate kindly, part of her glad for the interruption, while the other part completely disappointed. "Yeah, we have work early tomorrow, remember? Voight wants us in by 7:30."

"Oh, right. Well, I'll probably have a beer as my night cap then." Vanessa responds and the two partners laugh in mild shock.

"Yeah. I think I'm gonna head out, it's getting late. Take it easy there Rojas! Voight, bright & early, and hangover don't mix – trust me!" Jay laughs as he stands up passing Vanessa on her way to the reclining chair. "I'll see you tomorrow." He turns back to say to Hailey in a much different voice, the two sharing a heated look that hopefully Vanessa is too drunk to pick up on.

"Yeah, see you tomorrow…" she gives him a small smile before he exits the room and lets himself out.

Hailey starts grabbing their beer bottles to clean up as Vanessa watches. "I didn't interrupt anything, did I?"

"No!" Hailey quickly and adamantly responds. "Like he said, it's getting late; I just have to get to sleep soon."

"Alright. Hey Hailey, seriously though, you two have had sex, right? Because if you haven't, you definitely should!" Vanessa smirks up at her, while chugging the remainder of Jay's beer.

Hailey grabs one of the smaller pillows and chucks it at her roommate, shaking her head and rolling her eyes as she laughs. "Seriously Vanessa, go to bed! Also, a lady never kisses and tells!"

She looks back and smiles at her before entering the kitchen and heading up to her bedroom, leaving the younger officer open-mouthed and staring. Vanessa then laughs to herself and says aloud to the empty room, " _I knew it!_ " before taking the final sip of the old beer.

* * *

_[A/N: A slight little tribute to and loosely-based on 6x07. Thought it would fit in perfectly along with this story. Hope you're still enjoying the ride! What do you think, is their tension sexual? Thank you for all the lovely reviews and following along thus far. Also, I know I haven't updated "Feelings" in a bit, but I honestly haven't had the heart to with the last few episodes. Plus, so many awesome one-shots from other's have been done! I do promise to get back to it though. In the meantime, enjoy this and hope it finds you all safe & well! Next chapter will probably delve into their past again. Take care!]_


	6. Chapter 6

The end of year three of their army service found Hailey and Jay stationed in Germany for a few months. Luckily, the two of them had been placed in the same battalion and had been hopping around everywhere together. Unfortunately with the exception of a few months here or there, they had been separated from Mouse, Olivia, Bobby, and John. They missed them all, but not having them around just helped to reaffirm how close they were to each other. There were rumors that their unit's next destination was Kuwait, but nothing had been confirmed. Jay and Mouse had of course been thinking about applying for the Rangers for a while, but hadn't solidified it. For Jay, the thought of getting parted from Hailey physically hurt him. Her friendship was everything to him, and she felt the same way. They had been through a lot together the past three years, including Hailey's brief relationship with a fellow soldier that Jay thought was a douche and wanted to kill, and even worse, Jay finding out his mom got diagnosed with cancer and would have to go through her first round of chemo without him around.

Only Hailey knew how much of a sour subject it was family-wise for Jay. He already couldn't stand his father, but now he was starting to resent his brother as well. Jay was expecting Will to take a little break after Med school to go and be there for their mother since he couldn't, but Will was insistent that he had to take the job offer he got and that she should be fine with the original prognosis given. They had managed to get a few extra days of leave around the holidays that year and flew home to Chicago. Hailey didn't want to stop and see her family all that much aside from her brothers, so Jay insisted she spend Christmas with his. It started off great, since it was early in her treatment his mom was looking and feeling okay all things considered, and she loved Hailey. His dad spent most of the time drinking in the den by himself watching television, ignoring and barely acknowledging them at all, which had been fine with Jay. The three of them had a great Christmas Eve on their own. Things got rapidly worse the next day however when Will came home. The return of his favored son made Jay's dad come around them more, which only started Jay's simmering rage. Pat Halstead got progressively drunk at the dinner table and started berating his mom, as usual, despite her condition, which spurred Jay into confronting Will about not being around. The brothers got into a screaming match in which case their father took Will's side, and Jay stormed out, leaving Hailey to apologize. She tried to talk him into going back in, but he refused, knowing it was selfish, but would rather spend the next day (their last in town) with his mom without his father or brother around. So the two of them made the trek to Hailey's brother and sister-in-law's and spent the remainder of Christmas there. Jay apologized and hung out with his mom the next morning, and hasn't seen or heard from his dad or Will since. As for Hailey, she had made her brothers swear they wouldn't tell their parent's she had come back briefly. It had been an interesting holiday, but like everything else the past few years, Jay and Hailey were just glad they had each other.

It was now Summer and they had a few days of leave entitlement, so they set out to Munich to explore and unwind with their brief time off. When they arrived, they found out the hotel they had chosen was pretty booked and only had one room left. Since it was double-beds, they agreed to take it anyway, which left Hailey feeling a little nervous, but slightly elated. As close as they were, they had never been alone in a room together all night before, especially multiple days in a row. She didn't think too much of it though because they had a lot they wanted to do and wouldn't be in their room much anyway. That night they hit the local bars and drank well into the early hours, getting drunk on local beers and Jägermeister. By the time they made it back to their hotel, they were so exhausted and out of it that they didn't even realize they plopped and passed out on the same bed. When morning came they were so focused on getting out quickly to tour they didn't even have time to think about it. They spent the day touring a couple of different castles, Englischer Garten, and of course St. Peter's Church. It was just after they had finished dinner when the weather took a turn for the worse. A horrible storm was going to be passing through for the rest of the night. They debated riding it out in more bars, but instead decided to head back to the hotel since they were tired from the long day. They had Jäger in the room and it would allow them to get an early start on more touring in the morning.

They plopped on their beds for a bit with their drinks and watched a German channel that had English subtitles on it. After a bit Jay remembered something and quickly reached into his duffle bag, smiling proudly at Hailey as he pulled out a deck of cards. "I almost forgot I brought these! Wanna play?"

She smiled back, "Sure." She responded.

They decided to sit on the floor, figuring it would be easiest. "Want to start with Blackjack?" Jay asked.

"I'm not great at it, but why not? Not like we'll be getting to a casino any time soon."

"Well, welcome to Cesar's Halstead, where the dealer is the most attractive man you'll ever meet and the drinks are free!" Jay jokingly winked as Hailey rolled her eyes at him.

"Shutup and deal!"

The two played a few hands in amicable silence, as Hailey kept losing, getting slightly frustrated. "I told you I stink at this game."

"Oh c'mon, it's not that bad." Jay exclaims.

"Says you, who's winning!" she jerks her head at him with a funny death stare.

Jay laughs. "How about poker, we can play that next?"

She mulls it over for a bit, quietly thinking. "I haven't played in a while, but sounds good."

They're playing another round when Jay randomly asks, "So what's up with you and Hot Shot?"

Hailey's head pops up from her cards. "Matt?"

"Of course, who else?"

"What do you mean what's up with us? We stopped seeing each other a while ago, you know that."

"I saw you guys talking outside your bunker last week."

"And you're just asking me now?" Hailey says incredulously.

"I didn't want you getting pissed at me; you know how I feel about him."

Hailey grins. "Yeah you made that pretty clear while we were seeing each other."

"Do you blame me? He would sleep with any female in the barracks and then some!"

"Oh? Speaking of, what about the random girls you've paraded around the past year? And how's Abby by the way?" Hailey asks with an eyebrow raise as Jay blanches at the name. Abby was a fellow soldier in their unit that he had slept with a few times. "Don't think I didn't know."

"That's different; there was nothing serious between me and those girls. They knew it was all fun, including Abby. I just don't want to see you get hurt."

"Well Jay, if you must know he just came to return my book that he borrowed. I've made it clear to him we were over, and I appreciate the concern, but never would I have called what him and I had 'serious.'"

Hailey can't help but notice how that seems to please Jay and it just feeds her anxieties even more. Olivia's teasing words over the years playing in her head. If she's being honest with herself, it's become harder to bury the feelings she may or may not have for him anymore. Not only has he really starting to fill into his looks- gone was the goofy 21 year old boy she met, replaced by a more hardened 24 year old man, but also there was no one on the planet she was closer to. It was such a predicament because she knew their friendship was too important to risk screwing up, but she could no longer deny she felt more for him.

"Oh, well, good then." Jay responds breaking though her thoughts. They get awkwardly quiet for a bit, Hailey deciding to down more liquor when Jay finally speaks again. "So, poker?"

"Absolutely!" Hailey smirks, secretly plotting the game she'll play as she feels the alcohol start to kick in.

They play a couple of hands, Hailey letting Jay win each, when finally she suggests a change-up. "We should make this more interesting."

"Like gambling? I don't know, Hailey, how about you just give me your money then?" Jay jokes.

She smirks into her glass. "No, I was thinking more along the lines of strip poker?"

Jay almost spits out his drink. "What? Are you just offering to get naked for me? Because if that's the case I'll gladly just sit back and watch."

"You wish! Seriously, it will be fun. We've always joked about playing it!"

"Yeah, with everyone else…" Jay responds as she stares back adamantly. "Alright, it's your funeral, Upton!"

Hailey grins in triumph and Jay deals the first hand of their new game. A few minutes later Jay sees himself losing his shirt as Hailey gets a Four of a Kind. She smirks at him as he studies her questioningly. He takes another sip of his drink, not too suspicious yet. Next thing he knows, he's losing his belt when she gets a Full House. He groans as she just shrugs her shoulders at him. Hailey then somehow pulls off a Royal Flush and Jay's losing his jeans, now leaving him solely left in his boxers since he wasn't wearing any shoes or socks when the game started. He's shooting daggers at her now while he deals the next round and she tries to hold back her laughter.

"You set me up!" he finally exclaims, looking at his current shitty hand.

"Whatever do you mean, Jay Halstead?" she tilts her head innocently.

"Oh, don't give me that!"

"Is now the time to tell you that I used to play poker every week with my brothers and dad's friends at the diner when I was younger?" she grins victoriously.

"You are a jerk!" Jay laughs.

"Read them and weep… oh, and lose the boxers!" she says as she lays down one last Flush across the hotel floor.

"Oh no, you tease. You know full well I agreed to this because I thought you'd be showing skin." He rolls his eyes and jokingly pouts.

"That's a damn shame… Guess you should be better at reading my poker face." she responds without an ounce of caring.

"I'm not taking these off. No way, you played me. Security would be kicking you off the table!"

"For what? Being a high roller? Doubtful, Jay. Now come on, I won fair and square, drop trou!"

Hailey says as she reaches over teasingly to pull his boxers, but Jay grabs her wrist quickly, shooting her a look in warning, already feeling his reaction to her close proximity.

"Alright, fine. What if I even the score?" she challenges. And as she sees him heatedly study her, she crosses her hands down to her waist and pulls her shirt off without warning.

" _Hailey_ …" Jay manages to choke out, both hearing the yearning in it.

"Is this even enough? Or should I take off my bra too?" she whispers as she already releases the clasp, dropping it onto the floor.

Hailey's never seen Jay's eyes so dark, so full of lust, and she figures hers probably look the same. Before she can second-guess herself, she moves her hand near his boxers again and murmurs, "Better?"

She sees his resolve break and the next thing she knows he's grabbing her neck and pulling her lips to his. There's no hesitation, the kiss is instantly deep and heated, and she wraps her arms around him and yanks him to the floor on top of her. After a few minutes of their tongues and hands exploring, Jay pulls back a little. They take a second to catch their breath; Hailey's still catching in her throat as he stares at her so unbelievably adoringly.

"You mean so much to me, Hailey. Are you sure about this? Should we?"

"No…" she answers honestly, because neither of them really are, but she knows she's never wanted anything more in her life. "But you know what they say, What Happens in Munich, Stays in Munich!" she beams at him.

He smiles back before kissing her again. His mouth moves down her body, kissing his way to the waistband of her jeans before unzipping them and pulling them off. It leaves both of them only in their underwear now. He continues his assault and Hailey has to bite her lip from moaning too loud. As his fingers reach the elastic of her panties she suddenly pops her head up and leans back on her elbows.

"Not so fast, mister. You still owe me first…" her eyes roll to his waist as they both grin.

"Only if you deal this _hand_ and you're _flush_ against me…"

His says winking and they both have a good laugh until her hands are on him and Jay groans loudly before pulling their last barrier away. Now skin to skin they know there's no turning back from crossing the invisible line they've had for so long. And as Jay starts softly kissing her neck and she wraps her legs tightly around his waist, they know they don't care. Some lines were meant to be crossed. They spent long hours on top of their discarded cards before finally making it to the bed, only to spend longer hours through the early morning there. As for the remainder of their trip, they couldn't tell you what else Munich had to offer because all they toured was their hotel room for the next two days, and the second bed never got slept in at all…

* * *

_[A/N: Happy Sunday! Hope this dose of youngin' Upstead gets you through whatever the start of your week holds. Enjoy this little trip into more of their past. I wonder what happens next? Thank you again for sticking with this and hope you're all staying well! Oh, and HELLO FLIRTY UPSTEAD missing each other in the finale!!! I think my heart stopped for 30 seconds, seriously, so awesome! Give me season 8 ;) ]_


	7. Chapter 7

Another few weeks had passed since Vanessa came home that night interrupting Jay and Hailey's serious conversation. In a way Jay was glad, he still didn't know how to explain himself or even if Hailey wanted him to. They were finally in a good place again and maybe it wasn't wise to resurrect old wounds. The cases they had at work took enough tolls on all of their mental states. Jay was so happy Voight had brought Hailey on and made her his partner though. It was perfect timing and even though he's unsure if he believes in those things, he's starting to wonder if his boss was like a wise guardian angel. Hailey genuinely seemed happy to be around him again too, and he knew she trusted him more than most, she always had. Still, it was becoming harder for Jay to separate the feelings he has and always had for her. He knows he fucked up his shot with her all those years ago, and doesn't want to push her and destroy what they've built presently. So he'll be her partner and friend, that's all, and if she happens to want more, then he'll let her lead the way.

They had just wrapped a case of a high-up criminal kingpin that had fronted as their CI briefly; and most everyone was exuberant over the amount of players they were able to put behind bars from it. They were closing in the bullpen when the group started to make plans for the night.

"Anyone in to hit Molly's for the night?" Kevin asked the room.

"You know I'm down!" Vanessa and Adam both said at almost exactly the same time causing everyone to laugh.

"I'm cool as long as the ginger ale is flowing!" Kim replied.

"Yeah, I'm down for one drink." Jay chimed in and looked to Hailey.

She smiled softly to everyone and said, "I think I'm going to pass tonight. But definite raincheck for Friday!"

No one pushed her as everyone focused on grabbing their coats and heading out, but Jay continued to study her which he knew she'd notice.

"You want to stop by when you're done?" Hailey asked him quietly.

"I don't have to go at all. I'll just pick up a 6-pack and meet you at your place."

"No, no, you already told them you'd go. They may get suspicious if we're both missing, especially Vanessa. We don't want to start more rumors surrounding us." She says laughing.

Jay laughs casually. "Yeah, I guess that's true. Okay, I'll go for one and then head over if that's cool?"

"Sure, sounds good!" she says and squeezes his shoulder before she makes her way out the back.

Jay's certain he's never nonchalantly drank a beer so fast in his life. He's trying to enjoy the time with his friends at the bar, he really is. They're all joking and in great spirits, which is sometimes few and far between, but he'd much rather be spending his time with someone else. As exciting as it all was to wrap this case, he knows Hailey had struggled working it at times. She blamed one of the drug leaders for getting her best CI killed a couple of years ago, so she wasn't always thrilled with playing nice with such darkness. But that's just how it was; sometimes you had to deal with some hellhounds in order to help the bigger picture. Jay swallowed the rest of his pint and excused himself from the rest of them, moving fast with his goodbye before they could question or stop him.

As he was walking away he could hear Rojas go, "$20 says he's going to hang out with Hailey."

Followed by Atwater, "I'm in on that!"

All he could do was roll his eyes and smile as he pushed open the door, embracing the cold outdoors to head to his partner, old best friend, and whatever else they were or she'd let them be…

* * *

Jay showed up at Hailey's door with a pint of expensive whiskey and a 24-ounce bottle of craft beer. She was already in sweats by the time he got there and her smile grew wide when she opened the door and saw his gifts.

"Just what the doctor ordered!" she said to him as he walked inside.

"I aim to please!" he smiled back.

"That was pretty quick. Did you even go to Molly's?

"I did. Had a full beer and everything! By the way, I'm pretty sure Rojas knows I was coming here. I heard her collecting bets as I was walking away."

Hailey rolled her eyes as they went into the living room. "It figures. She's got this scandalous idea in her head of what our relationship is and she's always teasing. I think she's mostly kidding because she hates how close to the vest I keep my personal life and past."

"Somebody should clue her in that it takes a lot more than being your roommate to get to all of Hailey Upton's dirty secrets. Hell, I'd love to know more myself!" he teases.

"Shutup!" she laughs while shaking her head at him. "I think I've let you in plenty!"

Jay smirks, pressing his lips together to stop himself from commenting, but quirks his brow at her questioningly.

She hits him with a couch cushion as he cracks up. He still knows how to exasperate her, but in a good way. "You know what I meant!"

"Maybe. So we going to watch the Hawks or are you going to keep hitting me?"

She switches the hockey game on and they sit amicably for a bit just sipping their drinks and happy to be in each other's presence. After a while, Jay starts to study her again. He knows she's fine, at least as fine as can be, but he doesn't want her bottling anything in like he knows she does (they both do).

"You want to talk about it?" he finally asks her.

She turns to look at him and he doesn't have to say anymore because she already knows what he means. Their wavelengths have never wavered despite a decade apart.

"Not really. What's done is done." She gives him a small, reassuring smile.

"I know, but I just want to make sure you're okay."

"I'm fine, Jay. We got so many dangerous people off the streets and behind bars, that's all that matters right?"

"Yeah, but I also know you. And even though I wasn't around when he got killed, I'm sure there's a part of you that felt guilty you couldn't save him too."

"Of course, he wasn't perfect, but he was _my_ CI, Jay. His blood was just as much on my hands as it was on anyone else's. I should have done more to get him out of the game. But if it wasn't for his death a couple years ago, we wouldn't be where we are now. So many more criminals would still be roaming the streets, killing even more people. I've made peace with it, seriously. I would tell you if I hadn't." she squeezes his arm and nods at him.

Jay looks her over once more and finally decides she's telling the truth. The scar will always be scabbed over, but at least it's not bleeding anymore. "Just know that I'm here now, Hailey. I'll carry anything with you, like you've always done for me."

"I know, Jay." They smile softly at each other and sip their drinks again until Hailey switches gears. "So, Adam and Kim, huh? How long has that been going on?"

Jay laughs heartedly. "Who knows!? Those two have been on again and off again since they met. I can't keep up anymore."

Hailey chuckles along with him. "Yeah, Kim told me they were even engaged for a bit. I can't believe she's pregnant."

"Me either! Maybe this will be the thing that makes them shit or get off the pot."

"Always the romantic, Jay." They both crack up before getting serious again. "I don't know how she's doing it though. That's scary, being pregnant and coming into our kind of job every day…"

"Yeah, but if anyone can handle it, it's Kim." Jay responds honestly. "Do you ever think about it? You know, kids and settling down?"

He watches her hesitate for a bit before answering. "Of course… but you know, with the kind of history people like us have with our own parents, it's kind of hard to believe in the fairytale of it all. I'd want it one day, but it would have to be with the right person. I could never put my kids through what my parents did to me."

"Yeah, I get that…" he replies softly.

They get silent again, gently staring at the other as an almost awkward tension fills the room. The weight of the moment isn't lost on Jay, so he decides to drop another truth bomb on her.

"I think you'll be a great mom one day, Hailey."

He notices a flicker of awe in her eyes that arrives just as quickly as it goes, but she smiles tenderly. "And you'll make a great dad."

They let the conversation hang in the air for a while before focusing back on the game; neither wanting or ready to discuss it further. As Jay stares at the screen, the score bar implying the Blackhawks are losing, but not registering how, he contemplates for the millionth time bringing up their past again. Part of him wants to be the man that deserves her now, even though he didn't think he did back then. And unfortunately he proved it to be true. He knows he's ready now, but also knows she's holding that notion of them at arm's length again. He doesn't blame her. After weighing all options, he decides it's best to just let things be for now. He needs something else to distract him better though or he's going to rashly act, and he wants her to have the control. Little did he know she was having similar thoughts.

"This game is atrocious. Can we find something else?" he finally caves in the 3rd period.

"I have cards in my bedroom…" her tone suggestive.

"Hailey…" his jaw drops in shock as he stares at her incredulously.

"One time offer, Halstead. Take it or leave it!" she says getting up and looking back to him as she walks to the kitchen to put their glasses in the dishwasher then starts making her way to the stairs.

He watches her disappear up the steps as he tries to close his jaw from hanging open. Well Hell, she doesn't have to tell him twice! He quickly runs up the stairs, nervous but excited, and slightly unsure what to expect. When he reaches her room he finds her waiting by the bed for him, looking equally nervous, but also exuding sexual confidence that would make grown men make fools out of themselves for. He's seen them, heck, he's been one of them. He swears he's never come across a woman who could make even sweats look as ungodly sexy as she does. She communicates with her eyes and gives him a small nod. He turns around to close and lock her bedroom door then slowly makes his way over. When he reaches her he lets her have command and she puts her arms around his neck and pulls his lips to hers. The kiss is instantly passionate, but surprisingly tender, and it's as if no time has passed at all. They stand there making out for intensely long minutes, as Jay takes the time to relearn the inside of her mouth with his tongue. Finally, they break away breathless and stare at each other.

He rests his forehead on hers. "Hailey, are you sure about this?" his voice comes out husky from desire.

"No…" she says equally as raspy as they smile at each other, remembering this same conversation from the last time they were together like this.

She breaks away to sit on the bed, then grabs his shirt to pull him down on top of her. They start kissing again ending all second guessing for the remainder of the night. It's a while later when they fall asleep in each other's arms, well sated, and completely clear-headed for the first time in a while.

Jay wakes to the alarm on his phone going off at 5am. They had agreed he'd leave really early so there was no chance of Vanessa being awake yet and catching them. He groans, partly from the early hour, but also not wanting to let Hailey go. He kisses her forehead as she stirs peacefully before making his way to her master bath. He figured a quick shower would be good to wake him up for the early drive. He also needs the hot water to pound out the thoughts in his head. He has no idea what last night means for their relationship, but judging from Hailey's adamancy about him leaving before Vanessa would find out, he figures it was just a one-time thing. He can't help but let the disappointment seep in, even though he promised himself he'd let her take the lead. The last thing he wants to do is ever hurt her again, so if he really blew his chance from all those years prior, well then so be it. He's deep in thought when he hears the shower curtain pull back and Hailey steps inside with him.

"G'morning!" she smiles at him as she gives him a peck on the lips.

He doesn't even have a chance to question what's happening before she moves her lips down his chest and before he can even process what's happening, she's on her knees and taking him in her mouth. He has to bite into his lip hard to stop himself from grunting loudly, for certain he'd wake Vanessa if he let escape the pleasure Hailey was giving him. Instead he hits his head back against the wall and wraps his hands in her hair as she takes him over the edge.

Once he's done he watches her stand back up with a shit-eating grin on her face. "I didn't think you could be so quiet…" she whispers teasingly.

"You're asking for so much trouble, Upton!"

He grins back before he smashes his lips to hers and pushes her against the wall. As he moves his mouth expertly down her body he watches her bite her lip this time, so firm he's sure it might draw blood. He smirks proudly as he makes her stifle her screams three times. They've gotten so carried away that Hailey's 6:30 phone alarm is now going off in the bathroom with them. Luckily she brought it in on the off-chance they were called for a case.

"Shit." She exclaims as they both realize it's time to get moving.

It's still way too early for Vanessa to be up so they take a moment to tenderly dry themselves off before Jay throws his clothes back on. As he makes his way over to her bedroom door to let himself out, he's pleased to find her right behind him. She pulls him down and kisses him softly.

"Drive safe and don't forget my coffee." She whispers against his lips.

"Never!" he nods back before tiptoeing out of her room. He grins ecstatically as he quietly sneaks out of the house, _maybe he still has a chance after all_ …

* * *

_[A/N: I want to preface this by saying I'm so happy you guys enjoyed the last chapter. It's actually how I came up with the idea for this story... thought it would be cool to see them bond in the past, like in the army, and that strip poker would be a funny way to have their first time. Low and behold, this story arose. I don't question my mysterious thoughts these days, I just run with them, lol! On that note, hope you enjoy this chapter as well. Thank you as always for the support, and please stay safe & sane!] _


	8. Chapter 8

The day had come for them to leave Munich and for Jay that meant reality was setting in. He had spent the last two days in bed with Hailey and they had honestly been the best days of his pathetic excuse of a life. Every kiss, every caress, every whispered sentiment that they shared was embedded in his brain and he doubts he'll ever forget them. He's grateful for this because he knows he's going to need these memories to get him through reality. The reality being he knows he doesn't deserve her. He is so broken and she's gone through so much already, he'd never want to add on to her plate. And if he's being really honest with himself, he can't stand the thought of ever losing her. If they tried the romantic route and he screwed up, there was no coming back from that. But if he just stepped back, let the dust settle some, then their friendship still had a shot. He made up his mind that he would sign up for RASP (the Ranger Assessment and Selection Program) the second they got back. If anything, maybe it would help him work on becoming a better man for her. He kept repeating in his head so much that it was for the best that he almost believed it. He was deep in this thoughts while driving them back to base when he felt Hailey grab his hand he had resting on the console. She brought it up to her mouth and kissed the back of it. She was studying him, looking at him lovingly, as her lips quirked up into a small smile. It nearly broke his heart.

"Whatcha thinking about?" she asked.

He grinned back at her, trying to be reassuring. "Nothing. Just I can't believe we're heading back already."

"Yeah, it was a great time away. I needed to get rid of some tension." She gives him a subtle wink.

"Yeah." He tries his best to smile.

"You sure you're okay? _We're_ okay right? We don't have to put a name to what happened or anything, you know. We can just take things one step at a time." She tells him softly.

"I'm good. We're good. I'm just trying to wrap my head around going back…"

"Okay. But you tell me if something is wrong!"

"I will." He squeezes her hand reassuringly.

_I'm such a coward_ he thinks for the remainder of the ride. Luckily Hailey pulls out one of her mixed CDs and starts cranking it and singing along the rest of the way. It gives him an out with talking or explaining things, but seeing her like this, _so happy_ , it makes him fall for her even more. She deserves someone who can make her feel that way all the time.

When they get back to base, their routine picks back up almost instantly. It leaves Jay the perfect excuse to not have to see Hailey for the next day or two. They each had their own assignments and he could just keep pretending he was super swamped with his. In that time he reached out to Mouse and told him he finally made up his mind about the Rangers and that they shouldn't wait anymore and just do it. His friend found it a little suspicious that Jay was suddenly in a rush, but Jay didn't delve into any details as to why. He knows if Mouse found out what happened between him and Hailey he would try to talk Jay into going for it with her. He just couldn't risk it, this was the best move. By the time the third day their return from vacation arrived, Hailey had persistently been trying to see and talk to him. Somehow he managed to come up with an excuse each time, seeing her for no more than a few minutes here or there. He didn't have the heart to tell her he was shipping off back to the States due to his own accord at the end of the week. It killed him not so see her, but he truly convinced himself it was for the best.

By the time the end of the week rolled around and he was a few hours away from his flight to Georgia, he wrote a note for Hailey. He knew if he went to say goodbye in person he'd never be able to leave. He left the note with his Signal Officer, Kane, knowing Hailey would go to him when she realized he was nowhere to be found. He hadn't shared his departure with anyone else in the unit. By the time Hailey realized Jay was gone, he was already on the plane.

Hailey stormed into the office confused once she found all of Jay's belongings were gone from his bunk and no one seemed to know where he was. She ran up to Kane instantly.

"Hey, have you seen Halstead today? I haven't been able to get in touch with him for the past day." She asks.

Kane looked at her oddly. "He left for Fort Benning a few hours ago…"

"HE WHAT?" she gasps shocked.

"I assumed you knew… he's going to RASP. He left me this to give to you." Kane hands her the note.

"Thanks…" Hailey says confused as she grabs it and walks away, heading back to her barracks.

It's not until she's alone again, on her bed, that she opens the letter to read, and the tears start to fall.

_Hailey,_

_I am SO SORRY! I know you won't believe this now, but I did this for you. I'm too damaged, Hailey. Maybe the Rangers will make me a better man. A more worthy man for someone like you. I wrote this five different times until I finally decided that maybe short and simple was the best approach. I know you're going to be angry either way, and I don't blame you. I want you to know that our time in Munich meant everything to me, which is why I had to do this. I want so bad to live that fairytale with you, but I know in the long run I'd somehow find a way to hurt you worse than this. I hope we can be friends again one day. You'll always be my best one. Please take care of yourself! Your future is so bright and you deserve the whole world. I'm sorry I couldn't be the man you always saw in me, but maybe someday._

_Always, Halstead, Jay :)_

As Jay stares out the window of the plane, he reflects back on everything over the past week. And on his three plus year friendship with Hailey. All the perfect memories she game him just left him in anguish. He was selfish, really he was scared, and all he's known his whole life was running away to solve a problem. So that's what he did. He hoped it would make sense one day, but it never did. By the time he realized she wasn't a problem- that she was the best blessing he ever got, and that he wouldn't have screwed it up because she made him better, it was too late. And it was the biggest mistake he ever made because he lost the most important person in his life…

* * *

_[A/N: Thanks for all the love, truly y'all are the best. I don't know if you've noticed, but I've been speeding up Upstead some in my stories. I'm so over their slow-burn in the show and fics, it's been three years, it's time for something. And since we got a ways until the show returns that's what I've been doing, lol. Anyway, had to get this chapter out, had to happen, so it was time. Don't hate me or Jay too much! ;p Enjoy and take care of yourselves and each other!] _


	9. Chapter 9

It's close to two months now since Hailey initiated things with Jay that night after work when everyone else was at Molly's. She had fully intended for it to be a one-night thing, knowing she had to guard her heart and just hoping to get him out of her system once and for all. Unfortunately, her plan epically failed. Being with him again in that way was single-handedly the best experience of her life, but to put it in layman's terms, she knew she was screwed. Despite their now friends-with-benefit status or whatever it was, she's maintained keeping her guard up and trying to keep them from drifting into something past that. She could tell Jay wanted more, and even though she truly had forgiven him from their youth, she just couldn't risk it. Losing him had been awful. Wondering if he would even make it out of the Rangers alive had been worse. And she spent the better part of her early to mid-twenties trying to leave what they had in the past. She focused all of her energy on the army and the remainder of her unit, and when her tours finally ended there she focused it all on her career. She took pride in the fact she made Detective by the time she was 27. And slowly but surely she got over the immense pain of not having Jay in her life. It shifted to embers that were able to stay in her subconscious, only getting reignited if she poked them… which she tried never to do. So now that not only was he back in her life, and they had rebuilt their friendship, and then went another level again, she wasn't willing to risk losing the former due to _feelings_ and weakness. She knows she should probably just stop the sexual aspect of their relationship altogether, she just can't break away from the comfort it brings her yet. But she'll be damn sure to not allow it to go any further than that.

Speaking of Jay, it was late Saturday afternoon and she had told him she'd get to his place by seven for dinner. She was finishing up the last of her chores around the house when Vanessa came into the kitchen to grab a drink.

"Hey, my friend from Gangs and I are gonna check out that new bar in Bucktown tonight if you're interested?" her roommate asks her.

"Thanks, but I'm going to Jay's in a bit. Next time for sure!"

Hailey watches as Vanessa quirks her brow at her and gives a little smirk. She doesn't think anyone at work has been too suspicious of her "relationship" with Jay, aside from Vanessa who sees her (and him) more. They've been as professional as can be on the job, and even going out to drinks or whatever with the others, they always make sure to not be _too_ close or touchy-feely. They're convinced they're smart and that it's working, but really their coworkers have just been pretending to not know… after all, they're observant cops too.

"You've been spending a lot of time at Halstead's recently." Vanessa points out, casually fishing.

Hailey tries to hide her grin, not willing to give her roommate the ounce. "Yeah, we've been playing a lot of cards."

"Cards?" Vanessa questions.

"Yeah, I'm really good at Poker so I've been trying to give Jay some tips for when they have their Boy's Nights."

"Poker? Alright. I see you, Hailey. Well, if you guys get bored with you know, _playing cards_ , you know where to find me!"

Vanessa winks and runs out of the kitchen before Hailey can throw her cleaning rag at her. Yet another reason Hailey has been avoiding an _actual_ relationship with Jay… they work together, the odds of complications arising from it just possibly isn't worth the risk. At least this is what her head keeps telling her, which is what she intends to keep listening to. Her heart wants too much that she just isn't willing to give.

* * *

Hailey and Jay are sitting on his couch watching the game after dinner. They're sipping on their beers and just enjoying the downtime after a long week. He loosely has his arm draped around her and she tries not to lean into him too much. She's been avoiding cuddling as the weeks have gone on because that brings out more feelings in her than actually having sex with him does. Still, at the end of a long day or week all she craves is his embrace.

"So who is this Ronald Booth Voight mentioned you had to go to court for again? I read the file, he's just some Meth dealer, right?"

Hailey tenses under his arm and pulls back. She looks down into her beer bottle trying to avoid the subject, but senses Jay's eyes on her studying her.

"Yeah, he was this big drug dealer I brought down when I was undercover… no biggie. I just have to go and make a statement again so he won't get paroled anytime soon."

"Something tells me there's more to the story…" Jay responds softly.

"Jay…" she says slowly, hoping to get him to drop it.

"C'mon Hailey, you know you can tell me anything."

She sighs internally. She really has no desire to relive another portion of her past, especially that one. But they are partners now, and if there's one person she's always been comfortable opening up to, it's him.

"A couple of years into the job I got assigned this undercover case. It was an incredible and rare opportunity that was stressed to me wouldn't be easy because I'd have to be under for at least a year. I figured, _what the hell_ , you know? After everything with the army, this would be a piece of cake…" she says drifting off.

Jays stares at her intently. "Except it wasn't?"

"No, it wasn't… I went under with my partner, Garrett. They had us pose as a couple from Iowa. Things went well for the first few months until Booth started developing this obsession with me. He hated Garrett, but kept him around because he didn't want to risk losing me. We were under for almost a year when Booth made a trip to St. Louis around the holidays. He was there to talk to a major player the Feds were trying to ID. So New Year's Eve there was a party, Booth was drunk and I got him alone thinking I could get a name. He had other things in mind. He beat the shit out of me, would have raped and killed me if it hadn't been for Garrett coming in and pulling him off of me. A week later Garrett disappeared… we never found his body. But I knew Booth had killed him. I stayed under through the rest of January while we finally got enough evidence to bust him on the drugs. We were never able to pin Garrett's disappearance on him." She manages to surprisingly get it all out with ease and minimal tears. For some reason, sharing it with Jay is therapeutic. The empathetic way he's looking at her makes her heart swell.

"You loved him?" it pains him to ask, but he knows Hailey had a past after him just as much as he did.

She gives him a soft frown and a nod. "As much as I could anyway… he was there in a difficult time in my life when I couldn't turn to any of my friends or family, since I wasn't supposed to know any of them. Not that I had all that many by that point anyway. Olivia and Bobby were across the country, and I lost touch with most people from Chicago when we were overseas."

"I'm so sorry, Hailey. I'm sorry that you lost him. I'm sorry I wasn't there… I should have reached out again when I got home, but I…"

"It's okay, Jay. It was a long time ago." She reaches out to touch his arm.

"I'm going to go with you to the hearing."

"You don't have to do that!"

"You're my partner, of course I do."

She smiles gratefully at him. She was dreading doing this and reliving it all alone. "Thank you."

He leans over and kisses her forehead, pulling her into his embrace again. She wraps her arms around his waist and takes a moment to relish in the feeling. Her brain kicks in soon enough though, making her realize she doesn't want to get too lost in this. So she does what she's been doing for weeks and switches her emotions to physical again. She pulls back and moves her hands to his face before leaning up to kiss him. He kisses her back sweetly, but she doesn't want sweet. She can't handle it. Sweet doesn't allow her to guard her heart, so she deepens the kiss as she moves to straddle him, taking him by surprise.

Jay finally breaks away, panting and breathless. "Hailey, let's take a minute. We can talk some more."

She hungrily nips at his neck, moving her lips back up to his. "I don't want to talk anymore!" She says before kissing him passionately and grinding her hips into him. She feels him groan into her mouth and his resolve break as he suddenly stands up with her still wrapped around him. She feels her back hit the wall as Jay's mouth moves down her chest. Somehow they make it into his bedroom, leaving a trail of clothes along the way. Hours later while they've almost drifted to sleep, Hailey remembers her phone on his nightstand.

"Hey, can you grab my phone so I can set my alarm for 7:30? With Vanessa at the bar tonight she definitely won't be getting up before then."

"Hailey, you don't have to sneak out and get back to your bed. She knows you're here."

"Yes Jay, I do."

She watches his mouth open as if to say something more, then he silently closes it and lets out a sigh. He realizes there's no sense in arguing. And she realizes that he wants more than she can give. It's a continuous tug-of-war that she can't back down from… until it's too late…

* * *

_[A/N: We are reaching the homestretch, folks. Probably another couple chapters left of this story before I wrap it up. Hope it's keeping you on your toes. Thank you for all the support and love, it's forever appreciated. Take care and stay safe! And to anyone bringing us Upstead content in fics, edits, pics, etc, thank you! It's much needed during this drought.]_


	10. Chapter 10

It's been almost a year now since Hailey had joined Intelligence and close to four months since her and Jay had started sleeping together again. They developed a pattern; usually spending as much as five nights a week together, sometimes more. They normally split the time between houses. Usually Jay left hers early in the morning (or snuck out onto the couch) to not make Vanessa question them more, or Hailey would leave his to try to get back before she woke up. Hailey knew her roommate suspected them, especially with the relentless teasing, but Vanessa tried not to pry and Hailey didn't want to give up the façade. She was also pleased that Jay wasn't pushing for more, even though she knows he wants it. If she let herself be honest for once, she did too, but she was fearful for her heart. Trying to get over Jay once had been bad enough, she's not sure she could survive another. Plus, their friendship was everything to her, a relationship posed a threat to potentially lose it if things didn't work out. So they carried on and continued the silent agreement of not discussing what _they_ were too much.

Summer had finally arrived in Chicago and as excited as everyone had been for some warm weather finally, it was showing no mercy. They were in the middle of a July heat wave and temperatures weren't the only thing rising. Crime seemed to become even more rampant and people were losing their minds a little extra. The drug trade was running wild and the team was looking to bust one major dealer in particular, Hugo Chavez. He had been flipping trap houses in order to launder drug money. All of the work and renovations were being done by a subcontractor, Frank Lombardo that one of Adam's CI's knew. That's how the team had gotten the intel on how Hugo acquired so much more cash for purchase. They were going to round up Frank today and try to get him to talk.

"So my CI assures me that Frank frequents this deli on Belmont every Friday at noon. He's unsure if the owner has any involvement, but the family did have ties to the Chicago Outfit years ago. We should be able to grab Frank before Hugo has any idea as their meetings are normally Saturdays at one of the properties. I think we can have him talking by the end of the day. He's apparently a big family man and his wife just got popped for her second DUI a few weeks ago." Adam explains in front of the pin board while the whole team stands around listening.

"Alright, Ruzek and Rojas, you go grab up Frank. Atwater, Burgess, go stake out the 2nd property, make sure nothing pops. Halstead, Upton, I want you monitoring Chavez. He so much as breathes the wrong way I want him brought in today too. Let's go!" Voight orders out before heading back into his office.

The gang grabs their phones or whatever from their desks and start bounding their way down the stairs and out to their cars.

"You guys down to come over tonight for some pizza if this all goes well? Adam and I just bought one of those inflatable pools. It's my last week before desk duty!" Kim asks before they all go their separate ways.

"Now by inflatable pool, do you mean one of those baby ones Ruz likes to dip his delicate feet into, or like we'll all be able to wear bathing suits and not sweat to death?" Kevin jokes.

"You're not gonna be doing the back stroke in it Kev, but we can all fit. It takes chlorine and everything!" Kim responds matter-of-factly.

"I'm in. This heat is disgusting; I'll take any kind of water at this point!" Vanessa says excitedly.

"Sure, I'll bring the beer!" Hailey answers after sneaking a look at Jay that doesn't go as unnoticed as they think.

"Jay?" Kim questions.

"Of course. Let's get this day over with then. I'm not gonna be the only one who says no."

With now pleasing a pregnant Kim, they all quickly wave their goodbyes and hope for a good bust. Kevin whispers near her ear scoffing, "Pssh, he meant he's not gonna say no when Hailey already said yes!" Kim cracks up as they reach the car.

* * *

Less than a half hour later, Hailey and Jay are parked across the street from Hugo's house. It's all quiet as he appears to be just hanging inside. The two partners figuring it will be an easy day for them, especially once Frank is in custody.

"So… does this mean you're going to wear a bikini later?" Jay asks teasingly.

"Are you seriously asking me if I'm going to wear a bikini around our coworkers in a tiny inflatable pool?"

"It is 100 degrees out. I'm just trying to look out for your well-being." He grins at her while she rolls her eyes.

_Two can play this game_ she thinks. "How about I wear one after you drive me home from Kim's? I've been meaning to try the g-string one I didn't have the confidence to wear when I went to Greece." She looks at him as innocently as possible.

Jay's mouth gapes open speechless and he quickly reaches to lower the air conditioner even more. After getting his thoughts to settle for a minute, he finally responds. "You don't play fair, Upton!"

"You started it, I just simply had to finish." She shrugs nonchalantly as they both grin at each other before focusing on work again.

It's a little after noon now when they see Hugo moving in the living room window on the phone. He appears to be yelling at the person on the other end. Whoever he is talking to must have spooked him because suddenly he's staring at the window alight and looking directly at them, recognition and anger appearing on his face. Jay and Hailey obviously can't hear him, but it's apparent he's yelling profanities; then suddenly he's disappearing from view. They already know this is about to go sideways fast. Out of nowhere Hugo runs out of the house and over to his car, peeling out of the driveway like a bat out of hell.

"Shit! He made us!" Hailey exclaims as Jay's turning the ignition and popping a U-ey with his pickup to follow.

"5021 George, fleeing offender in black Land Rover down Abbott, plain-clothes officers in hot pursuit, requesting backup…" Jay hollers into his radio.

Hugo is speeding and weaving fast through the pedestrian neighborhood. Jay is driving just as manically to catch up as Hailey hangs on to her handle bar. She suddenly recognizes the area and realizes he's making his way to his other property.

"Kev, he's coming your way." She radios out to alert Kevin and Kim.

Hugo pulls down the garage street to the back of the other house and is running into it when Jay and Hailey arrive. They rush out of their vehicle guns drawn wondering why he'd come here when Kevin comes running around the corner of the house to meet them. Hailey shot Kevin a questioning look in reference to Kim's safety which he understood.

"Yeah, she's staying in the car." Kevin says as they hear the backup squad car arrive.

Jay's the first one to breach the house followed by Hailey and Kevin when they hear the hollering coming from down the stairs. They slowly make their way down when they hear Hugo loud and clear.

"I swear to God I will blow her brains out!"

They arrive at the bottom of the basement apartment to see Hugo holding his gun to some girl's head. The girl is both equally frantic and pissed.

"Put down the gun, Hugo, there's no way out of this." Jay tries to tell him calmly as he approaches him from the front while Hailey slips by to cover from the side and Kevin stays aimed from the stairs.

"Don't come any closer or she dies!" Hugo exclaims.

"What the fuck, Hugo? Let me go! You didn't even call in the warning!" the girl screams back.

"Calm down, alright, everyone just calm down. Miss I need you to stay quiet. Hugo, you're about to be surrounded, just let her go and we can figure this all out at the district. No sense in adding murder to your plate." Jay tries to reason.

"I'm not stupid, having her hostage is the only thing keeping you guys back. I knew I couldn't trust Frank!"

Hugo is sweating profusely, and acting manic, having nothing to do with the heat. They can tell he's tweaking. They know they need to get out of this situation and fast. Jay gives Hailey a side-eye when Hugo shifts slightly and he knows he has a shot, Hailey nods back in understanding. Jay shoots his gun, hitting Hugo by his neck and the man falls back and drops to the floor.

After that everything happened so fast. Jay started to move in to grab him, but none of them had realized that the girl had a small firearm in her shirt pouch. As she looked down at Hugo and started screaming she pulled it out before any of them could even realize it and shot Jay in the chest. It was Hailey's turn to scream then as Kevin shot the girl from the stairs and Hailey started running over frantically to Jay's fallen body. Everything around her started to spin and she felt like she was in a muffled tunnel where time seemed to be going at rapid speed, but also somehow in slow motion. She registered Kevin screaming, "DROP THE GUN!" and patrolmen flying down the stairs and into the room with them. She recalls staring into Jay's watery eyes, pale and drooping trying to stay open, and her hands on his chest placing pressure, so much blood in-between them. She hears Kevin, or maybe it was one of the other cops, requesting ambulances, going off about one of their own. And through her tears she remembers saying things like, "Stay with me, Jay!" She can feel the paramedics surrounding them now and she registers that suddenly Kim is in the room with them, trying to comfort her and pull her back. The last thing she remembers of the chaos is still putting pressure on Jay's wound even while he's on the gurney and they're lifting him outside and taking him to the ambulance; then clear as day telling Kim and Kevin, "I'm going with him!" And then all she hears is the onslaught of sirens as the ambulance and all the squad cars speed down the streets to the hospital while her sobs almost suffocate her.

* * *

It's been hours now as the team and Trudy sit in Med's waiting room anxiously awaiting any news on Jay. The room is full of patrolmen; all worried about one of their own. The seat next to Hailey is like a musical chairs game as each Intelligence member gives it their best to try to comfort her. She appreciates the effort, but she can't focus on anything until she gets news of Jay. She doesn't want to drink, eat, or talk. She just wants to know that the most important person in her life will be okay. Finally, on hour three Will Halstead enters the room and Hailey pops up to hear what he has to say, as everyone else does the same. She's the first to him and he directs a warm smile specifically to her. He looks like he aged ten years since she last saw him a few weeks ago. But for some reason it takes her back to months before when she saw him for the first time again at Molly's. Jay had asked him to come when a group of them all went out, he wanted Hailey to meet him again under better circumstances than how she saw the brothers years before. Hours into their night of laughs, Hailey and Will had found themselves away from the others while at the bar ordering more drinks. And what the older Halstead said to her was something she'd never forget.

_"My brother must have really loved you, you know? He never told me what had happened between you guys, and I never felt like it was my right to ask. But for him to have brought you home that Christmas—the way things between him and my dad were and mom being sick, I knew you must have been very special to him. He would not have allowed you around that, us, otherwise. So I just want to thank you for being there for him some of those years when I wasn't. I really appreciate it, because I honestly don't know if he would have survived without you…"_

The memory brings even more tears to her eyes, but she tries to push them back and focus on what he's saying now.

"Hey everybody. I just talked to Dr. Marcel. He said the bullet grazed an artery; they're still trying to repair it."

"Will, is he gonna be okay?" Hank asks.

Will looks at them sadly, not wanting to be too somber, but also not wanting to ignite potentially false hope. "He's lost a lot of blood…"

Hailey fights back more tears as they nod at each other. Will squeezes her shoulder gently before addressing them all again. "I have to get back. I'll let you guys know the second I hear something more."

Hailey feels Kevin pull her into a hug before they make their way back to the seats again. As much as they all wanted to hear news, they're now wishing they hadn't. Kim sits next to Hailey and puts her hand comfortingly atop hers.

"I should have come in with you guys, I'm sorry!" Kim states sadly, the day catching up with her along with her guilt of not being able to help more.

"Kim, don't be silly. No extra bodies would have helped, and Jay would never forgive himself if something happened to you or the baby. Voight only sent you to that location because it was supposed to be the least dangerous. I don't know how it all happened, it was all so fast. I should have never let Jay or any of us pursue him without vests…"

"No, Hailey, you guys did it right. No one could have predicted his hostage would be just as crazy." Kim tries to assure her now.

"Yeah…." She agrees, drifting off, her voice getting even softer. "I just can't lose him…"

"I know. And you won't! If anyone can pull through this, Jay can!"

Kim sits with her for a little longer until Voight rounds most of the team up. Apparently Hugo is out of surgery and ready to talk, while Frank waits in lockup back in the district. He divvies the team to each to get some answers while he personally heads off with Trudy to the hospital room of the girl who shot Jay. More hours tick by as Hailey lets herself get lost in all her memories of Jay while waiting for more news, praying for it to be good. She gets a text from Adam alerting her that Hugo apparently ran to the second property because that's where his girlfriend, the one who shot Jay, had hid all the money. If they feared they were to be caught, she was supposed to snatch it up and light the house on fire to destroy all the evidence. Hugo botched it all in his drug-induced haze and took her hostage instead. And even though he held her at gunpoint and threatened to kill her, she wanted revenge on Jay thinking he had just killed her boyfriend. It was true, love really did make people crazy.

Around dinner, with the team finally getting all their suspects and the case closed, they started making their way one by one back to the waiting room. Vanessa was the first to arrive back.

"Hey, how are you?" Vanessa asks as Hailey hops up to give her a quick hug.

"I'm alright." She responds quickly, at a loss for what else to say.

"I got you some gyro from Greek Islands, thought you might be hungry."

"That's really sweet of you, thanks."

"And I got you some clean clothes from the apartment."

Hailey smiles at her gratefully. "Thank you." She responds, her voice coming out slightly hoarse from her sadness.

"Have we heard anything about Jay?" Vanessa asks as she takes the seat next to her again.

"No." she shakes her head at her roommate.

She takes a beat and then she starts to talk about Jay, needing to assure herself again that he'll be fine and cherishing having a moment to have someone listen again.

"He's gonna freak out when he wakes up, the man hates needles. I can't figure him out. He's the first one through the door… a war vet, and he'd rather take a bullet than get the flu shot." She scoffs and bows her head again, getting emotional over her memories of Jay.

"Hailey…" Vanessa starts to say and pauses, seeming to choose her words wisely. "I know how hard this must be for you…"

Hailey quickly tries to deflect. "Of course, it's Jay. It's hard for all of us."

"But it's harder for you because you love him…" Vanessa bluntly says, the words hanging in the air.

Hailey looks away a second, then smiles sadly. She's not ready for _this_ conversation, at least not with Vanessa. If she's being honest, her whole problem with Jay is she hasn't been ready for this conversation for more than a decade now. Through their entire time in the army, she tried to fight how she really felt about him. He was the first and only person in her life that she could truly open up to and be herself around, past warts and all. She can't help but to think now maybe if she was honest with him then, he would have never left. She could have made him realize how right for her he was. She didn't need him to be a better man, he was already the best one she knew. But that didn't happen, and now she realizes she might be making the same mistakes again. Her heart was broke and she hadn't been ready to admit or accept her true feelings for Jay. But she vows to herself she will if he's okay. And he HAS to be okay because she's not losing him again. So she gives Vanessa the one thing she can right now, a statement that Jay already knows to be true… anything more than that she owes him to be the first to hear it from her.

"Of course I love him, he's my best friend!.."

* * *

_[A/N: Alright, don't kill me, but of course I had to throw in a little AU ode to 7x9/10. I promise to make this outcome different in a good way... I think! ;) Anyway, hope you enjoy this one. I appreciate you all so much. Stay well and keep all the Upstead feels coming!]_


	11. Chapter 11

Jay wakes to a dull throbbing in his shoulder and the soft sounds of machines beeping near his ears. It takes him a moment to realize where he is and once he does the memories of what had happened wash over him. He had been shot by a hostage during what should have been a simple takedown. Oh well, he's glad to take the bullet if it meant Hailey, or even Kevin didn't. Right as her name pops through his head he senses movement to the right side of his hospital bed. He turns slightly to see Hailey looking over him with the biggest smile on her face, remnants of tears in her eyes and her hair pulled back haphazardly in a pony tail while she stands there in her favorite comfort hoodie. He can see the relief in her expression and dare he think it… the love? Once she realizes how alert and focused on her he is she starts to speak.

"Hey, how ya feeling?"

"Like I've been asleep for a year." He jokes.

"You needed a little rest." She beams at him.

"Hailey…" he begins as she tilts her head at him, like she already knows what he's going to say. "You know I hate hospitals."

"I do…"

"You gotta get me out of here!"

"Not optional, no." she laughs at him.

"Fine. Well then at least tell me you brought your bikini?"

She chuckles heartedly and his heart warms at the sound so much that he doesn't even feel the pain in his chest anymore. "Nice try, buddy."

"Oh come on, I was shot… the least you can do is let me stare at your sexy body if you won't let me leave."

He watches her blush and is pleasantly surprised when she leans down and lightly strokes his hair. His biggest shock comes when she rubs her thumb over his cheek and kisses him. The moment is quick but immense to him because he knows how many people they know are in this hospital with them right now. Any one of them could walk by and see and Hailey didn't care. He smiles, maybe the tides have turned after all.

"I'll put it on so you can take it off once you're cleared to get out of here..." She whispers against his lips and he feels his heart race. Her expression changes from happy flirtation to one of sadness though right after. "As long as you promise not to scare me like that again. I won't be able to bear it."

He wipes a tear from her eye with his thumb and holds her face steady in his hand. "Hailey, I'm here, and I'm alright. It's gonna be okay. I'm not leaving you again, ok?" he tries to assure her even if he can't make promises like she wants in their line of work. But he'd be damned if he left her without a fight, physically or emotionally.

He's rubbing her cheek and calming her a little longer when they hear a group of voices coming their way. "How's our favorite idiot patient doing?" they hear Trudy say.

"You know Jay, if you didn't want to come over you just had to say so. Getting shot is no excuse." Kim chimes bubbly.

"How you doing kid?" Voight's gruff voice carries over the other two.

Jay and Hailey turn their heads and smile as the whole group plows into the room. Along with the aforementioned, Kevin, Adam, and Vanessa were all there as well. Jay's never felt more loved, but even he feels like they're a little confined.

"What did you all flash your badges and bribe a nurse to come in here at the same time?" he asks while laughing.

"About that, it pays to be the brother of the kindest and best-looking doctor in all of Chicago. I can let some rules slide for my favorite police team." Will pops in and chimes behind them all.

They all share a laugh, glad to be having such a lighthearted moment when less than 24 hours ago they weren't sure if Jay would make it. While Jay stares at everyone he considers family, he realizes he's still holding Hailey's hand from before and she doesn't seem to care or be pulling away; nor is anyone else staring at them oddly or questioning the behavior. It's as if it's just common knowledge and nothing amiss. He uses the realization as an opportunity to give her hand a squeeze and she turns to smile at him as Kevin relays the story of how Hugo sounded like a scared little boy once he started coming down from his high.

"So Will, when do you think Jay can come back to work? I know he's going to be bugging me every day about it until he's back." Voight asks once Kevin finishes.

"All things considered, my brother got very lucky. There's no structural damage to the shoulder and Dr. Marcel was able to repair the artery with minimal intrusion to anything else. He's going to be sore and need physical therapy for a while, but he should be cleared for desk duty in another week. Active duty? Depending on how his recovery is going, maybe a week or two after that." Will addresses them all.

"Oh good, so I'll get a nice little break from him." Hailey jokes and they all laugh, happy to see her in good spirits again.

Jay rolls his eyes. "Please! You know I'm the best partner you ever had. Besides, who else is going to bring you coffee every day?"

"Vanessa has got me coffee before, and Kevin…" Hailey smiles.

"It's true bro, I have. I get coffee for all the ladies sometimes." Kevin says.

"He does!" Kim says as her, Trudy, and Vanessa nod their heads.

"What the fuck man? You never even brought me coffee from the break room!" Adam looks at Kevin incredulously.

"You don't look as good as they do, Ruz!" Kevin shrugs his shoulders.

When all their chuckling dies down some, Will steps in again. "Alright, I hate to break up this party, but it's gonna be my ass if someone catches all of us in here. And besides, my stubborn brother needs his rest."

They all say their goodbyes to Jay and give him and Hailey hugs with promises to stop by- at different times- tomorrow. Even Will steps out assuring him he'll swing by again once his shift is over. Soon enough Jay is left alone with his favorite person once more.

"Funny, I didn't see anyone expect you to leave." He grins at her as she pulls her chair closer to his bedside so they can relax and watch some TV.

"As much as I joke, you're stuck with me and they all know it. So you may as well just accept it, Halstead."

"I wouldn't have it any other way!" he replies as he links his fingers through hers again.

* * *

A few days later and Jay is ecstatic to finally be free of the hospital. Hailey had picked him up to take him home just a few short hours ago. They picked up Bartoli's on the way because he was absolutely sick of hospital food, even if it was only three days worth. They ate on his couch in comfortable silence. Hailey reaching over on occasion to help him if he found he couldn't balance a drink and a bite at the same time with the sling on. It was very domesticated and felt even more emotionally potent than their original friendship did all those years prior. He could feel that something had shifted between them again since he got shot, but he couldn't pinpoint it exactly. He just knew Hailey was more embracing of them, publicly and privately. He had been waiting for months for this moment, not wanting to push her. He realized they had to go at her pace after how he left things years ago. So he had been doing the best that he could just to show her how much she meant to him and earn all her trust back again. Who would have known that all it would have taken was a brush with death? Had he known that maybe he would have put himself in harm's way six months ago.

When they were done with their pizza and finally somewhat digested of the savory deep-dish, he sensed Hailey studying him. She was leaning against the other end of the couch with her legs draped over his lap. He could tell she was debating on saying something to him, so he raised the remote and lowered the television. She shifted positions, sitting up more so she was closer to him and tucking her legs under her body.

"Listen, um, when you were in surgery, no one knew what was gonna happen, and it made me realize that I wanted to tell you something…" she starts softly.

He stares back at her, recognizing the same look she had on now as the one she had when he woke up in the hospital. Only minus the relief this time, he's certain all he sees reflecting in her eyes is love. He's so sure he'd actually bet her in Poker on it. He feels an overwhelming giddiness take hold of his body, a feeling he's only had a few times in his life- shortly after meeting her when they were practically just kids and he knew she would be someone forever important to him, when he first got to kiss her when he was 24, seeing her for the first time again in Voight's office a year ago, and lastly when he got to finally kiss her again months ago. He knows he's no saint, there had been a lot of women before, in between, and after her, but none of them made him feel like Hailey did. Not even Erin had as much as he tried. So he holds his breath and grins a little, trying to contain his excitement and simply saying "Okay…" still ready and willing to wait for her.

"You were always the most significant person in my life, Jay. I've confided in you more than I have my own brothers. I know we weren't ready to take that step all those years ago. We were so young and the uncertainty of army life was no place to start a serious relationship. But our friendship was everything to me. So when you left for the Rangers without even giving me the heads up, another piece of me broke inside. It took me a while to get over it even though I could never get over you. And I tried, I did, but no matter who came along you were embedded in my soul. So when Voight reached out to me I took it as a sign, maybe the fates wanted us to cross paths again. And I'm so happy we did because as Vanessa so eloquently put it while I was crying in the hospital wondering if you'd survive- it was hard because I love you. And she was right, I do. I love you, Jay. You're my best friend and my favorite partner, but it's more than that because I'm so in love with you. And I'm finally telling you now because I can't lose you again."

She exhales deeply, as if a massive weight has finally been lifted from her shoulders. Then she just tilts her head at him and waits as he feels himself start to grin at her like an idiot. _Finally!_ He thinks. He grabs her hand and pulls her closer to him as he leans in so their faces are only inches apart.

"Hailey, you have no idea how long I've been waiting to hear you say that. I don't know what I did to deserve this second chance, but I promise you a lifetime of earning it. I never should have left the way I did back then, I just got so scared. My life was a mess and I thought I'd be saving you the trouble of having to constantly pick up the pieces of it. But I was an idiot and just missed you terribly all the time. And when I finally got back home and thought of contacting you again, by then my mom was real sick and my whole focus became her. And then after she died, I just couldn't reach out to you again because I wouldn't be able to handle potentially losing someone else I loved with my whole heart. Because I did, and I do. I love you so damn much! I'm so sorr-"

He's about to continue, try to express regret even more for back then, but Hailey cuts him off, kissing him passionately. He feels her hands hold his face to hers, neither of them willing to part until finally they have to break away to breath. They stare at each other while panting, theirs eyes filled with affection.

"You didn't have to apologize more. We're good, and we're always gonna be good!" She whispers against his lips, much like at the hospital.

He grins and starts kissing her again, wondering how he got so lucky for someone like her to come into his life. Not once, but twice.

She pulls back once more. "I do have something else I want to tell you…" Her voice raspy.

"Oh yeah?" he quirks his brow at her, quite curious at her seductive tone.

"I just might be wearing that bikini I promised under my clothes…"

She practically purrs out while gently pushing him back and leans up to undo the zipper on her jeans and shimmy out of them. He knows his eyes must be bugging out of his head as he grabs her with his good arm and pulls her on top of him. She lets out a little yelp as he feels her smile against his lips before he silences her again with his. Jay had always been a fast learner, but even he's impressed with how fast it took him to get her shirt off with one arm in a sling. He wonders what else he can learn tonight because he has years worth of time he wants to make up for and he intends to start right now…

* * *

_[A/N While this does seem like a conclusion and very well can be, I do intend to have a bit more to this story. Not sure yet if it will be one or two chapters longer, but their journey in this universe doesn't end here. Thanks for still following along and hope each and every one of you is doing well!]_


	12. Chapter 12

About a month later Jay was fully recovered and back to work as if nothing had happened. Things were great in Intelligence, but not as great as Jay and Hailey were, inside and out of it. Neither of them had ever been happier and they were both so thankful they finally admitted their feelings and took that official next step. It had been a long time coming! All of their coworkers had been ecstatic for them and also saw it coming from a mile away. The veterans had never seen Jay so positively happy and even Vanessa who had only met both of them a little over a year ago could attest that they were over the moon for each other.

With everyone's spirits so high recently, Hailey and Vanessa decided to have the crew over for a small hangout. It was one of those rare timse where the Cubs and White Sox were playing each other and their TV was just as good as a crowded bar's. The night had been a blast so far since Kim, now six months pregnant, opted to be the designated driver for Adam and Kevin. And of course Hailey, Jay, and Vanessa wouldn't be traveling anywhere. Needless to say, the drinks were flowing.

Adam was telling everyone the story of how he wanted to test how well his new jock cup was working one day, so Jay had offered jokingly to help assist. They went out back behind the district and Jay thought it would be funny if he karate kicked him in the groin, giving the full effect.

"So this asshole decides to kick up with all his might right into my junk!" Adam exclaims

"YOU TOLD US THE CUP WAS FULL-PROOF! You were the one bragging you wouldn't feel a thing!" Jay laughs along with everyone trying to defend himself.

"As you can guess, the advertisement had been wrong. I buckled to the floor and couldn't breathe. I had to ice my shit the whole night."

"I helped him up before I ran to get everyone else, but I do wish we had filmed it. He splattered to the ground like pancake batter."

"It was so funny! Even Voight started snickering when he saw Ruz with his ice pack." Kevin says.

"It was the first and only time Adam didn't want to have sex!" Kim jokingly chimes in.

"Yeah, yeah, yeah! So warning to all of you, don't buy stuff on a late night infomercial, especially when it claims to protect such an important and delicate part of your body." Adam responds.

"Hence why we've never taken any of Ruzek's suggestions for new vests." Jay explains.

Everyone cracks up and drinks some more, random stories surfacing from all. When the laughter and talking starts to slowly die down, Vanessa wants to try to keep the night still going.

"Hey Hailey, why don't we play some poker since you're always teaching Jay?" she asks, just trying to suggest a game.

Hailey and Jay almost spit out their beers, recognizing their secret code word instantly. Adam and Kevin both loudly scoff. "Wait, you mean to tell me Hailey _teaches_ you poker and you're _still_ terrible?" Kevin addresses Jay.

Vanessa watches Hailey blush as Jay tries to cover her tracks. "What can I say? I'm a work in progress, and really was just using it as an excuse to see this one more!"

Hailey watches as realization triggers in Vanessa's eyes and her roommate silently goes "OHHH!" to her before sipping her beer and trying to stay quiet. At least Hailey now knew what to say to her roommate if she wanted complete alone time with Jay.

"It's really a hopeless cause teaching Jay a good poker face, but he's learned a lot of valuable tips when we play alone." Hailey smirks while Jay smiles smugly and Vanessa's eyes go wide.

"You must strip for him when you teach him because this boy doesn't retain a thing when he plays with us. Or maybe you should start. He's embarrassingly bad!" Kevin says.

"I'll be sure to keep that in mind!" Hailey responds with a sly wink, making everyone start to wonder about their lessons together.

"I'm not sure I want to know, but I am envious of any sex life that doesn't involve a bloated bun in the oven for nine months." Kim jokes.

"Hey, our sex life has been awesome these past few months!" Adam exclaims.

"Aaaaand I think that's the cue for 'good night!'" Jay tries to get out straight-faced as everyone cracks up.

Within an hour later Kim was rounding up her two drunken passengers and all were saying goodbye. Vanessa stumbled over to her room after they left and Hailey and Jay maintained the energy to straighten up a little before heading upstairs. It had been a successful night and they all needed the laughs and hopefully work-free weekend.

Once they reached the confines of Hailey's room, Jay grabbed Hailey and pulled her back against him causing her to yelp lightly. He softly started to kiss her neck making her shiver delightfully. He slowly moved his mouth upward, whispering in her ear. "You know, I really liked Kevin's suggestion of you stripping for me again."

Hailey laughed lightly. "Oh, did you? Well if memory serves me right, you're usually the one stuck stripping."

"That's fine too. I enjoy ripping your clothes off myself."

Jay practically growled in her ear as he spun her around before yanking off his shirt and unbuttoning his jeans, making no show of it. She smiled as she slid her hands up his bare chest before settling them around his neck and pulling him down for a deep kiss. When that became not enough Jay gently threw Hailey onto the bed before yanking her pants off in succession. Then he climbed on top of her and slowly slid her shirt off as well. Hailey moved her hands down to his hips and swiftly pulled down his jeans and boxers too, copping a feel along the way.

Jay grinned against her lips after moving his up her body. "I thought I had to strip my own off."

"Faster this way, plus it lets me explore more!" she mumbles against his mouth before they start kissing again.

It's not long before what little bit of clothes left was swiftly removed and both forgot the hows and whys of who took off whose. The teasing quickly turned into soft moans and it was a while later when they finally caught their breaths again. Jay wrapped his arms around Hailey as she lay on his chest both completely blissful and satiated. They were both exhausted, but wanted to enjoy a little bit more of this absolute peace before succumbing to sleep.

"Mmm, do you ever think we should have gotten our shit together sooner? Imagine all the additional years we could have had this?" Hailey whispered as she lightly moved her finger back and forth along his ribcage.

"I know this is infinitely better than all the dreams I used to have of being with you completely. We're just going to have to make up for all the lost time." He responded, pulling her closer to give her a soft kiss.

"For sure."

"You know my mom got so mad at me when I told her we weren't talking anymore. She truly believed you were the one for me." Jay smiled at her in complete adoration causing Hailey's heart to ache with love.

"I always thought she was a smart woman." She said as she brought a hand to his face and cupped his cheek, this time kissing him.

Jay groaned as the kiss went on longer than either intended. "If you keep this up we're never going to sleep."

"You did say we had to make up for lost time…"

"I guess I'm pretty smart too…" he grinned while swiftly pulling her under him, catching a quick flash of her laugh before kissing her fervently. It definitely was a good thing they had off tomorrow.

* * *

_[A/N: Wow, this may be one of the longest times I've gone without posting since I started writing Upstead fic. Sorry for that. The world's been nuts & I tried to disconnect in nature; also I couldn't decide if I wanted to update this or do some kind of one-shot. But here is a little something to hold you guys over before the conclusion to this story. Thank you for everything and for all the kind words always. I hope everyone is staying safe and above all being kind to your fellow humans. Hopefully my next post is sooner next time. Until then, take care of yourself and others!]_


	13. Chapter 13

_10 Months Later_

Hailey and Jay walked into the church hand in hand. Hailey was wearing a pale yellow Spring dress and low heels, simple, but she looked beautiful regardless. Jay was in nice khakis and a button-down polo that matched his eyes. They really made business-casual look like so much more. They saw the back of Trudy and Mouch's head and made their way over to sit next to them in one of the first few pews. Everyone was so excited to be celebrating such a happy day when each day isn't given in their line of work.

"Well don't you two clean up nice!" Trudy commented in her normal teasing drawl as they sat.

"Thanks Sarge, you guys look great too!" Hailey replied.

"I never thought I'd live to see the day my little Kimmy and Ruzek were finally all mature and grown-up. Dressing nice for it was the only option."

"This must be a joy for you with all the shit… uhh…" Jay's eyes go wide and he mouths an apology towards the statue of the Crucifix when he remembers where he is, while Hailey hits him playfully and both women smirk. "I mean with all the _smart advice_ you didn't hold back giving them all these years. Plus, don't lie, that baby is now the apple of your eye."

"Yeah it's true, you all know I hold a soft spot for each of you, there's no need for me to say it… Anyway, there's some bets going on at the district that you guys are next in line for camp baby. I have $50 on next Christmas and we all know how ornery I get when I lose money, hint hint."

Jay and Hailey roll their eyes, but both laugh. "We'll keep that in mind." He responds as he links his hand with Hailey's again.

"Guys, don't let her fool or bully you, if or whenever you have a kid she's going to spoil them rotten." Mouch chimed in and everyone grinned in agreement.

A couple minutes later the church filled even more and Voight and Vanessa found their way into the pew with them, as well as a few other first responders across their huge work family. Adam and Kim came into the front of the church through a side room with Kevin and Kim's sister in tow. The latter of the two had been named the Godparents. Kim had given birth to an adorable and healthy baby girl 7 months prior and they were so thankful everyone would be able to see her baptized. They had named her Alice, and not only was she the apple of Trudy's eye, she was for everyone. Alice made even Voight softer and Hailey and Vanessa swoon. Even the men of Intelligence found themselves cooing around her. It was nice to have such innocence around a work life of darkness.

After the service everyone made their way back out to their cars so they could head over to the restaurant to gather and celebrate little Alice. The end of Spring had brought an exceptionally sunny day. That of which made the ring on Hailey's left hand sparkle and reflect causing her to smile as she opened the door to Jay's truck.

Instinctively she ran her right fingers over it as they got in the car. She turned to Jay grinning when she noticed him watching her. "I'm still not used to it."

Jay grinned back as he brought her hand up to his mouth and kissed it. "Well you better get used to it; you only have six months before another band gets added to it."

_For Hailey's birthday towards the end of Winter in late February, they decided to get out of the blistering Chicago cold and take a trip to California to visit Olivia and Bobby. It had been a few years since Hailey saw them and for Jay it had been over a decade. Despite the number of years, it was like no time had lapsed for the old friends. They were enjoying every minute of the week they spent there, so thrilled they finally found some time to take some of their furlough days. They enjoyed playing with Olivia and Bobby's rambunctious kids. The four of them had double date nights when Olivia's parents could babysit. They got to be the diligent tourists, Jay having only been out to California briefly once when he was a teenager. They celebrated Hailey's birthday with a huge ice cream cake. But best of all was the fact that they didn't have to worry about being called off to some gruesome crime._

_On one of their first nights there, Olivia pulled Hailey to the side to speak with her privately. The men were distracted by their beers and the game on TV._

_"_ _I'm so glad you finally bought a back scratcher and decided to scratch your itch for good!" she smirked at Hailey, referencing their long ago conversation._

_Hailey rolled her eyes at her and smirked back. "You're insufferable, you know?"_

_"_ _Yeah, but you love me anyway. And besides, you know I'm right. As much as Jay pissed me off for how he left things with you back then, maybe it wouldn't have happened if you jumped his bones sooner like I told you to."_

_"_ _You know what they say Liv, 'Everything Happens for a Reason,' and things have worked out so perfectly now, so maybe this was always how it was meant to be." Hailey reasons philosophically._

_"_ _You're right. And any guy that gets your ass out to visit me is the right one in my book. Plus, I called you guys when we were teenagers, so I should get special mention in the stories that get told to your grandkids!"_

_They both crack up before Hailey continues. "Oh, and like I didn't call you and Bobby getting together?"_

_"_ _Sure, but we never tried to fight off attraction or play the best friend card like you and Jay!"_

_"_ _Alright, touché, you win. I'll give you all claim to being all-knowing in the future. Now come on, my beer is getting warm!"_

_"_ _You just want to go back to sitting in Jay's lap!" Olivia teased while Hailey turned around to grin at her as she walked back over to the guys. Once Hailey made herself comfortable on top of Jay again, she winked at her old friend, allowing her the satisfaction of always being right._

_On their last night the four of them went out to a nice dinner. When it was wrapping up they had intended to move onto a dessert place, but Olivia said her and Bobby should head back because her mother texted that their daughter was being fussy._

_"_ _That's okay, we'll come with you. It's our last night." Hailey told her friend._

_"_ _Actually Hailey, I was thinking we could grab our dessert and hit the beach one last time. When's the next time we'll get to be by the ocean? We'll see the kids at lunch tomorrow." Jay cut in._

_"_ _Jay, we live right on a Great Lake." Hailey balks._

_"_ _It's not the same and you know it."_

_"_ _Yeah Hailey, you two should go enjoy some alone time. We'll see you tomorrow before you leave. Don't let us old married shlubs hold you back." Bobby chimes in._

_"_ _My husband speaks the truth. I'd kill for a moonlit beach walk without screaming children!" Olivia jokes._

_Hailey notices Jay giving the other couple a stern look, as if trying to signal something to them, but Olivia clearly ignores him. She doesn't read too much into it because soon she's realizing they're all right. She'd love for a quiet and romantic stroll with Jay to end their perfect vacation._

_"_ _Alright, well I'll text you tomorrow when we're going to head over." Hailey finally agrees and they all say their goodbyes._

_Minutes later Jay and Hailey are ordering homemade ice cream from a small shop Olivia had been raving about and the two walk out to the beach with it. It's a weeknight and they're not in a tourist area, so the beach is peaceful and private as they walk along the edge of the waves. Jay eats his cone with his left hand while his right is intertwined with Hailey's as she does the reverse._

_"_ _I can't believe this week is over. It went too fast." Hailey breaks the silence._

_"_ _Me either. This has been the best trip of my life." Jay confides in fervor._

_"_ _Yeah? Better than Munich?" she teases._

_"_ _Well, that will always hold a special place in my heart. I hadn't come so many times since I was a young teenager alone in my room and found my dad's Playboys."_

_She swats at him and playfully kicks him as they both crack up. "But seriously, any trip with you and just every day with you in general brings such joy to my heart that I never thought could exist." He confirms._

_"_ _Me too!" Hailey replies quietly, her emotions and love bubbling over._

_By the time they finish their ice cream, they stumble across an abandoned blanket with a couple of lit candles in the middle. Hailey stares at it confused, wondering who would leave this behind and why, but Jay just grins knowingly and pulls her towards it._

_"_ _Sit" he says to her, signaling with his hand to get on the blanket as he makes his way down._

_"_ _What? Jay, what's going on?" she asks when she finally sits due to his prodding._

_"_ _We've never been one for big declarations, our silent communication trumps all. So I'm not going to switch that up just for this. Hailey, I love you with everything I have and I know you know that. And I know you feel the same way about me. I foolishly lost you once before and I never intend for that to happen again. I'd follow you anywhere. Home is where you are and that's where I always want to be, I never want to run again…"_

_Jay pauses and Hailey gasps when she sees him pull a ring box out of his pocket and shift on his knee. Her hands instinctively cover her mouth in shock as slow tears of happiness glaze over her eyes._

_"_ _Hailey, will you please marry me? There's no one else I want by my side for the rest of my life!"_

_"_ _Ye, yes!" she manages to gasp out as she leans forward to kiss him, holding onto his face like it's her lifeline._

_When they finally pull away he slips the ring on her finger and they hug each other tightly. A minute later Olivia and Bobby come running out from the dark cheering in excitement. Hailey and Jay laugh along with them and stand up to embrace their friends._

_"_ _You knew?" Hailey asks Olivia in amazement._

_"_ _Of course! And you almost destroyed the surprise. Wanting to end the night and come back to our place. When did you become such a lameass?"_

_"_ _You gonna call out Hailey when you two talked so much shit of marriage and kids at the restaurant to get her to agree for us all to split up?"_

_"_ _Oh shutup Halstead, Jay! It got her here didn't it?"Olivia sasses back._

_"_ _Alright, this is definitely going down as a vacation for the record books!" Hailey beams._

_"_ _Better than all the sex in Munich?" Bobby asks._

_"_ _You told her?" Jay asks Hailey._

_"_ _You told him?" Hailey asks Olivia._

_Both women just shrug and start laughing as the guys shake their heads._

_"_ _This is what you're in for. You sure you're ready buddy?" Bobby jokingly asks him._

_"_ _I've been ready since the day I met her. I was just too dumb for too long to do anything about it. But I've never been happier than to be here now." Jay passionately exclaims._

_Hailey smiles and wraps her arms around his neck before she kisses him again. Olivia and Bobby take that as their cue to slip away and leave the lovebirds to themselves, knowing that very shortly they're going to try to compete with their Munich record…_

* * *

Once their battalion got stationed overseas Jay, Hailey, and Mouse made it out for a bar night the first chance they were allowed. Since Jay and Mouse were 21-year olds in the States, Hailey was the only of them who hadn't gone out for a legal drink yet. But they intended to rectify that tonight.

"I'm gonna get us like 10 beers, than we can have a chugging match. What better way to ring in your first true bar experience?" Mouse exclaims.

"What? That's a horrible idea, no way. Besides, Hailey wants an Old Fashioned." Jay stares at Hailey waiting for her confirmation.

"He's right." Hailey nods back at Jay.

"You guys are no fun. But fine, we'll start with liquor." Mouse says dejectedly as he makes his way over to the bar.

Once he's there Jay notices his buddy eyeing up the redhead a few seats away and he can't help but to chuckle to himself.

"What's so funny?" Hailey asks curiously.

"He's so gonna get plowed and try to sleep with her tonight."

"Oh God, I'm leaving you in charge of getting him back to base."

Jay raises his brow at her. "And who's going to get me back?

"Maybe if you're lucky you'll get the redhead to." Hailey jokes.

"Ehhh, she's not really my type. Plus, she probably doesn't speak a lick of English. I like knowing what's coming off someone's tongue before I come on it…" Jay plays back.

"Oh my God! Remind me again why I agreed to come out with you guys tonight?"

"Because you love us. Me more than Mouse of course, but we'll keep that between us."

"Keep it up, Halstead and I just may leave you two to fend for yourselves. I'm sure I can find something other than goofballs in this bar to hang out with."

Jay puts his hands to his heart in mock hurt and they're both still grinning when Mouse comes back with the drinks.

"I just found my future wife!" he says surprisingly animated for still being sober.

"Told you!" Jay says to Hailey and they crack up. Mouse rolls his eyes at them, well used to not being in the loop on their continual inside jokes by now.

Their night continues on with drink after drink. All of them knowing this will be few and far between of them getting to have down time like this and not knowing what the future of war will entail; or if they'll even make it through it. Hailey had finally agreed to switch to beer a couple in and they did do a chugging contest. Jay won of course and naturally used the opportunity to gloat. Despite the amount of alcohol being consumed, both Hailey and Jay tried to maintain, while Mouse did get plowed.

"Seriously, I'm going to marry that girl and she's going to father my five children. I mean she'll mother them!" Mouse slurs out.

"You want FIVE kids?" Jay gapes learning this new information about his friend.

"Yeah! Who wouldn't? How many do you guys want?"

"Two." Jay and Hailey both say in unison, sharing one of their looks at the shock and trying to hide their blush.

"Aww, how cute! Maybe you'll have them together! If so I think I should be the Godfather of the second one."

Jay and Hailey share another look, a flicker of wonder in their eyes, but neither dare say a word. They don't need to complicate things by going there. But it's a nice thought to have.

"Alright dude, I think it's time we get you back…" Jay says while pulling Mouse up from the table as Hailey helps despite his protests. When they both reach around Mouse's back for better leverage, their hands accidently graze each others. They both feel the spark and quickly pull apart, willing any feelings that don't involve them being _just friends_ away. Little did they know fate had other plans for them…

16 years later their next journey started with the first kid, making Trudy's bet a winner when the birth of their son was born. After all, that's what happens when fates collide…

* * *

_[A/N: Here we are, the final conclusion to this story. Hope the timelines in this chapter make sense. It's also a little cornier than I like, but I guess we could all use some fluff at the moment. Thank you so much for going down this journey with me. I really enjoyed writing Jay & Hailey this way. It was a fun ride and I'm so happy you guys seemed to enjoy it too. I appreciate you all. I think I'll be going back to one-shots for a bit, maybe even do a prompts, so stay tuned. Until then, hope you all stay safe & take care!] _


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